Substitued arylketones

ABSTRACT

The invention relates to novel aryl ketones of the formula (I)  
                 
 
     in which  
     A 1 , A 2 , Q, R 1 , R 2 , X, Y and Z are as defined in the description,  
     their use as herbicides and processes and intermediates for their preparation.

[0001] The present invention relates to novel substituted aryl ketones,to a process for their preparation and to their use as plant treatmentagents, in particular as herbicides.

[0002] It is already known that certain substituted aryl ketones haveherbicidal properties (cf. EP-A-090 262, EP-A-135 191, EP-A-186 118,EP-A-186 119, EP-A-186 120, EP-A-319 075, EP-A-352 543, EP-A-418 175,EP-A-487 357, EP-A-527 036, EP-A-527 037, EP-A-560 483, EP-A-609 797,EP-A-609 798, EP-A-625 505, EP-A-625 508, EP-A-636 622, U.S. Pat. No. 5804 532, U.S. Pat. No. 5,834,402, U.S. Pat. No. 5,846,906, U.S. Pat. No.5,863,865, WO-A-95/31466, WO-A-96/26192, WO-A-96/26193, WO-A-96/26200,WO-A-96/26206, WO-A-97/27187, WO-A-97/35850, WO-A-97/41105,WO-A-97/41116, WO-A-97/41117, WO-A-97/41118, WO-A-97/43270,WO-A-97/46530, WO-A-98/28981, WO-A-98/31681, WO-A-98/31682,WO-A-99/03856, WO-A-99/07688, WO-A-99/07697, WO-A-99/10327,WO-A-99/10328, WO-A-00/05221 and in particular WO-A-00/21924). However,the activity of these compounds is not entirely satisfactory.

[0003] This invention, accordingly, provides the novel substituted arylketones of the formula (I)

[0004] in which

[0005] A¹ represents a single bond or represents O (oxygen), S(sulphur), SO or SO₂,

[0006] A² represents alkanediyl (alkylene), alkenediyl or alkinediyl,

[0007] Q represents O (oxygen) or S (sulphur),

[0008] R¹ represents hydrogen or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl,aryl or arylalkyl, or represents the grouping —C(Q)-R²,

[0009] R² represents hydrogen, amino, cyanoamino, nitroamino,hydroxyamino, hydrazino, or represents in each case optionallysubstituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio,alkylamino, dialkylamino, alkoxyamino, N-alkyl-alkoxyamino,alkylhydrazino, dialkylhydrazino, alkenyl, alkenyloxy, alkenylamino,alkenyloxyamino, alkinyl, alkinyloxy, alkinylamino, cycloalkyl,cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy,arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,

[0010] X represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl,

[0011] Y represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylamino, dialkylamino or dialkylaminosulphonyl, and

[0012] Z represents one of the groupings below

[0013] where

[0014] m represents the numbers 0 to 6,

[0015] R³ represents hydrogen, halogen or represents in each caseoptionally substituted alkyl, alkylthio or aryl, or—if m represents2—optionally also together with a second radical R³ represents oxygen oralkanediyl (alkylene),

[0016] R⁴ represents hydroxyl, formyloxy, halogen, or represents in eachcase optionally substituted alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy,aryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy,arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio,arylalkylsulphinyl or arylalkylsulphonyl,

[0017] R⁵ represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,or represents in each case optionally substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkoxycarbonyl or cycloalkyl,

[0018] R⁶ represents hydrogen or represents in each case optionallysubstituted alkyl, alkenyl, alkinyl, cycloalkyl, cycloalkylalkyl, arylor arylalkyl,

[0019] R⁷ represents hydroxyl, formyloxy, or represents in each caseoptionally substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy, alkylsulphonyloxy, alkenyloxy, alkinyloxy,arylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxy,

[0020] R⁸ represents hydrogen, cyano, carbamoyl, thiocarbamoyl, halogen,or represents in each case optionally substituted alkyl, alkylcarbonyl,alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl,

[0021] R⁹ represents hydrogen or represents in each case optionallysubstituted alkyl or cycloalkyl,

[0022] R¹⁰ represents hydrogen or represents in each case optionallysubstituted alkyl or cycloalkyl, and

[0023] R¹¹ represents hydrogen, cyano, carbamoyl, halogen, or representsin each case optionally substituted alkyl, alkoxy, alkoxycarbonyl,alkylthio, alkylsulphinyl or alkylsulphonyl.

[0024] The radical X is preferably located in position (2) of the phenylring.

[0025] In the definitions, the hydrocarbon chains, such as alkyl oralkanediyl, are in each case straight-chain or branched—including incombination with heteroatoms, such as in alkoxy.

[0026] If the compounds of the general formula (I) can exist indifferent stereoisomeric forms, the invention includes thestereoisomeric forms possible in each case.

[0027] Preferred substituents or ranges of the radicals present in theformulae listed above and below are defined below.

[0028] A¹ preferably represents O or represents a single bond.

[0029] A² preferably represents alkanediyl (alkylene), alkenediyl oralkinediyl having in each case up to 6 carbon atoms.

[0030] Q preferably represents O (oxygen).

[0031] R¹ preferably represents hydrogen, represents in each caseoptionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkyl-sulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl,alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino havingin each case 1 to 6 carbon atoms in the alkyl groups, representsdialkylamino having in each case 1 to 4 carbon atoms in the alkylgroups, represents in each case optionally cyano- or halogen-substitutedalkenyl or alkinyl having in each case 2 to 6 carbon atoms, representsin each case optionally cyano-, halogen- or C₁-C₄-alkyl-substitutedcycloalkyl or cycloalkylalkyl having in each case 3 to 6 carbon atoms inthe cycloalkyl group and optionally 1 to 4 carbon atoms in the alkylmoiety, represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogeno-alkoxy-substituted aryl or arylalkyl having in each case6 or 10 carbon atoms in the aryl group and optionally 1 to 4 carbonatoms in the alkyl moiety, or represents the grouping —C(Q)-R².

[0032] R² preferably represents hydrogen, amino, cyanoamino, nitroamino,hydroxyamino, hydrazino, represents C₁-C₄-alkylcarbonyl, representsC₁-C₄-alkoxy-carbonyl, represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylamino,alkoxyamino or alkylhydrazino having in each case 1 to 6 carbon atoms inthe alkyl groups, represents dialkylamino, N-alkyl-alkoxy-amino ordialkylhydrazino having in each case 1 to 4 carbon atoms in the alkylgroups, represents in each case optionally halogen-substituted alkenyl,alkenyloxy, alkenylamino, alkenyloxyamino, alkinyl, alkinyloxy oralkinylamino having in each case 2 to 6 carbon atoms, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl,cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy orcycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-or C₁-C₄-alkoxy-carbonyl-substituted aryl, arylcarbonyl, aryloxy,aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl,arylalkoxy, arylalkylthio or arylalkylamino having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety, or represents in each case optionally nitro-, cyano-,halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted monocyclic or bicyclic heterocyclyl,heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,where in each case the heterocyclyl grouping contains up to 10 carbonatoms and additionally at least one heteroatom selected from the groupconsisting of nitrogen (N) (but at most 5 N atoms), oxygen (O) (but atmost 2 O atoms), sulphur (S) (but at most 2 S atoms), SO and SO₂ andalso optionally additionally one group selected from the groupconsisting of oxo (C═O), thioxo (C═S), imino (C═NH), cyanoimino (C═N—CN)and nitroimino (C═N—NO₂).

[0033] X preferably represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallycyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl-or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups.

[0034] Y preferably represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallycyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl-or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups.

[0035] Z preferably represents one of the groupings below.

[0036] m preferably represents the numbers 0 to 3.

[0037] R³ preferably represents hydrogen, halogen, represents in eachcase optionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl oralkylthio having in each case 1 to 6 carbon atoms, or represents phenyl,or if m represents 2—optionally also together with a second radical R³represents oxygen or alkanediyl (alkylene) having 3 to 5 carbon atoms.

[0038] R⁴ preferably represents hydroxyl, formyloxy, halogen, representsin each case optionally cyano-, halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy or alkylsulphonyloxy having in each case 1 to 6carbon atoms, represents in each case optionally halogen-substitutedalkenyloxy or alkinyloxy having in each case 3 to 6 carbon atoms,represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-halogenoalkylsulphinyl-,C₁-C₄-alkylsulphonyl- or C₁-C₄-halogenoalkylsulphonyl-substitutedaryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy,arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio,arylalkylsulphinyl or arylalkylsulphonyl having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety.

[0039] R⁵ preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1to 6 carbon atoms in the alkyl groups or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms.

[0040] R⁶ preferably represents hydrogen, represents optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally cyano- or halogen-substituted alkenylor alkinyl having in each case 3 to 6 carbon atoms, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkylor cycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-halogenoalkylsulphinyl-,C₁-C₄-alkylsulphonyl- or C₁-C₄-halogenoalkylsulphonyl-substituted arylor arylalkyl having in each case 6 or 10 carbon atoms in the aryl groupand optionally 1 to 4 carbon atoms in the alkyl moiety.

[0041] R⁷ preferably represents hydroxyl, formyloxy, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkoxy,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy oralkylsulphonyloxy having in each case 1 to 6 carbon atoms in the alkylgroups, represents in each case optionally cyano-, orhalogen-substituted alkenyloxy or alkinyloxy having in each case 3 to 6carbon atoms, or represents in each case optionally nitro-, cyano-,halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-halogenoalkylsulphinyl-,C₁-C₄-alkylsulphonyl- or C₁-C₄-halogenoalkylsulphonyl-substitutedarylalkoxy, arylcarbonyloxy, arylcarbonylalkoxy or arylsulphonyloxyhaving in each case 6 or 10 carbon atoms in the aryl group andoptionally 1 to 4 carbon atoms in the alkyl moiety.

[0042] R⁸ preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, alkylcarbonyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl having ineach case 1 to 6 carbon atoms in the alkyl groups.

[0043] R⁹ preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, or represents optionallycyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6carbon atoms.

[0044] R¹⁰ preferably represents hydrogen, represents optionally cyano-,halogen- or C₁-C₄-alkoxy-substituted alkyl, or represents optionallycyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6carbon atoms.

[0045] R¹¹ preferably represents hydrogen, cyano, carbamoyl, halogen, orrepresents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atomsin the alkyl groups.

[0046] A² particularly preferably represents methylene (—CH₂—),ethane-1,1-diyl (—CH(CH₃)—), ethane-1,2-diyl (dimethylene, —CH₂CH₂—),propane-1,1-diyl (—CH(C₂H₅)—), propane-1,2-diyl (—CH(CH₃)CH₂—),propane-1,3-diyl (—CH₂CH₂CH₂—), butane-1,3-diyl (—CH(CH₃)CH₂CH₂—),butane-1,4-diyl (—CH₂CH₂CH₂CH₂—), ethenediyl, propenediyl, butenediyl,ethinediyl, propinediyl or butinediyl.

[0047] R¹ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, bromine-, methoxy-,ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, methylamino, ethylamino, n- or i-propylamino, n-, i-, s-or t-butylamino, represents dimethylamino or diethylamino, represents ineach case optionally fluorine-, chlorine- and/or bromine-substitutedethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl, butinyl orpentinyl, represents in each case optionally cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl- or propyl-substituted cyclopropyl,cyclobutyl, cyclopentyl, cyclohexyl, cyclopropylmethyl,cyclobutylmethyl, cyclopentylmethyl or cyclohexylmethyl, or representsin each case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, di-fluoromethoxy-or trifluoromethoxy-substituted phenyl, naphthyl, phenylmethyl,phenylethyl, naphthylmethyl or naphthylethyl or represents the grouping—C(Q)-R².

[0048] R² particularly preferably represents hydrogen, amino,cyanoamino, nitroamino, hydroxyamino, hydrazino, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino,n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino,ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino,methylhydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- ort-butylhydrazino, represents dimethylamino, diethylamino,N-methyl-methoxyamino, dimethylhydrazino or diethylhydrazino, representsin each case optionally fluorine-, chlorine- and/or bromine-substitutedethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl, butinyl,pentinyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio,butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino,propenyloxyamino, butenyloxyamino, pentenyloxyamino, ethinyl, propinyl,butinyl, pentinyl, propinyloxy, butinyloxy, pentinyloxy, propinylamino,butinylamino or pentinylamino, represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl- orpropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino,cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino,represents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,trifluoromethoxy-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted phenyl, phenylcarbonyl, phenoxy,phenoxycarbonyl, phenylthio, phenylamino, phenylhydrazino, naphthyl,naphthyloxy, naphtylthio, naphthylamino, phenylmethyl, phenylethyl,phenylmethoxy, phenylethoxy, phenylmethylthio, phenylethylthio,phenylmethylamino, phenylethylamino, naphthylmethyl, naphthylethyl,naphthylmethoxy, naphthylethoxy, naphthylmethylamino ornaphthylethylamino, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, difluoromethyl-, trifluoromethyl-,dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-,fluorodichloromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, n-, i-, s-or t-butoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-,difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted monocyclic orbicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino from thegroup consisting of furyl, furyloxy, furylamino, furylmethyl,furylmethoxy, furylmethylamino, thienyl, thienylmethyl, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolylmethyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl(oxazolinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl),tetrahydroisoxazolyl (isoxazolidinyl), oxazolylmethyl, thiazolyl,dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl),thiazolylmethyl, thiazolidinyl, oxothiazolidinyl,cyanoiminothiazolidinyl, oxotriazolinyl, oxotetrazolinyl, piperidinyl,piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl,2-oxo-1-aza-cycloheptyl, 2-oxo-1,3-diazacycloheptyl, morpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy,pyrimidinylmethyl, pyrimidinylmethoxy.

[0049] X particularly preferably represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine,or represents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,dimethylaminosulphonyl or diethylaminosulphonyl.

[0050] Y particularly preferably represents hydrogen, nitro, cyano,carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine, iodine,or represents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,dimethylaminosulphonyl or diethylaminosulphonyl.

[0051] m particularly preferably represents the number 0, 1 or 2.

[0052] R³ particularly preferably represents hydrogen, fluorine,chlorine or bromine, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, or represents phenyl, or—if mrepresents 2, —optionally also together with a second radical R³represents oxygen, propane-1,3-diyl or butane-1,4-diyl.

[0053] R⁴ particularly preferably represents hydroxyl, formyloxy,fluorine or chlorine, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methoxy, ethoxy, n- ori-propoxy, methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy,represents in each case optionally fluorine-, chlorine- and/orbromine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,represents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-,difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-,ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl-,ethylsulphonyl- or trifluoromethylsulphonyl-substituted phenyloxy,phenylthio, phenylsulphinyl, phenylsulphonyl, phenylcarbonyloxy,phenylcarbonylalkoxy, phenylsulphonyloxy, phenylmethoxy,phenylmethylthio, phenylmethylsulphinyl or phenylmethylsulphonyl.

[0054] R⁵ particularly preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine or bromine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, or represents in each case optionally cyano-,fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl.

[0055] R⁶ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally cyano-, fluorine-, chlorine-or bromine-substituted propenyl, butenyl, propinyl or butinyl,represents in each case optionally cyano-, fluorine-, chlorine-, methyl-or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-,difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-,ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl,ethylsulphonyl- or trifluoromethylsulphonyl-substituted phenyl orphenylmethyl.

[0056] R⁷ particularly preferably represents hydroxyl, formyloxy,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy, ethoxy, n- ori-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, or represents in each case optionally cyano-,fluorine-, chlorine- or bromine-substituted propenyloxy, butenyloxy,propinyloxy or butinyloxy, or represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, difluoromethylthio-,trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-,trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl- ortrifluoromethylsulphonyl-substituted phenylmethoxy, phenylcarbonyloxy,phenylcarbonylmethoxy or phenylsulphonyloxy.

[0057] R⁸ particularly preferably represents hydrogen, cyano, carbamoyl,thiocarbamoyl, fluorine, chlorine or bromine, or represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl.

[0058] R⁹ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, or represents in each case optionally cyano-, fluorine-,chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0059] R¹⁰ particularly preferably represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n-or i-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, or represents in each case optionally cyano-, fluorine-,chlorine-, methyl- or ethyl-substituted cyclopropyl, cyclobutyl,cyclopentyl or cyclohexyl.

[0060] R¹¹ particularly preferably represents hydrogen, cyano,carbamoyl, fluorine, chlorine or bromine or represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl.

[0061] A² very particularly preferably represents methylene (—CH₂—),ethane-1,2-diyl (dimethylene, —CH₂CH₂—) or propane-1,3-diyl(—CH₂CH₂CH₂—).

[0062] R¹ very particularly preferably represents hydrogen, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-,methylthio-, ethylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n- or i-butyl, represents methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n-or i-propylamino, represents dimethylamino, represents in each caseoptionally fluorine- and/or chlorine-substituted propenyl, butenyl,ethinyl, propinyl or butinyl, represents in each case optionally cyano-,fluorine-, chlorine- or methyl-substituted cyclopropyl, cyclobutyl,cyclopentyl, cyclohexyl, cyclopropylmethyl, cyclobutylmethyl,cyclopentylmethyl or cyclohexylmethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-,methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy- ortrifluoromethoxy-substituted phenyl, phenylmethyl or phenylethyl, orrepresents the grouping —C(Q)-R².

[0063] R² very particularly preferably represents hydrogen, amino,hydroxyamino, hydrazino, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-,ethylthio-, n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methylthio, ethylthio, n- or i-propylthio, methylamino, ethylamino, n-or i-propylamino, methoxyamino, ethoxyamino, n- or i-propoxyamino,represents dimethylamino, represents N-methyl-methoxyamino, representsdimethylhydrazino, represents in each case optionally fluorine- and/orchlorine-substituted ethenyl, propenyl, butenyl, propenyloxy,butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino,ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino orbutinylamino, represents in each case optionally cyano-, fluorine-,chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl,phenylamino, phenylmethyl or phenylethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, difluoromethyl-,trifluoromethyl-, dichloromethyl-, trichloromethyl-,chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, difluoromethylthio-,trifluoromethylthio-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl orheterocyclylalkyl from the group consisting of furyl, furylmethyl,thienyl, thienylmethyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl,pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, imidazolyl,imidazolylmethyl, 2-oxo-1,3-diazacyclopentyl, oxazolyl, isoxazolyl,oxazolylmethyl, isoxazolidinyl, thiazolyl, thiazolylmethyl, piperidinyl,oxopiperidinyl, 2-oxo-1,3-diazacyclohexyl, morpholinyl, piperazinyl,pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl.

[0064] X very particularly preferably represents hydrogen, nitro, cyano,fluorine, chlorine, bromine, iodine, methyl, ethyl, n- or i-propyl,difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl,methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.

[0065] Y very particularly preferably represents hydrogen, nitro, cyano,fluorine, chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.

[0066] m very particularly preferably represents the number 0 or 1.

[0067] R³ very particularly preferably represents hydrogen, representsin each case optionally fluorine- and/or chlorine-substituted methyl,ethyl, n- or i-propyl, methylthio, ethylthio, n- or i-propylthio, orrepresents phenyl, or—if m represents 2—optionally also together with asecond radical R³ represents oxygen, propane-1,3-diyl orbutane-1,4-diyl.

[0068] R⁴ very particularly preferably represents hydroxyl, representsformyloxy, represents in each case optionally fluorine- and/orchlorine-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl, ethylsulphonyl, acetyloxy, propionyloxy, n- ori-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n-or i-propylsulphonyloxy, represents in each case optionally fluorine-and/or chlorine-substituted propenyloxy, butenyloxy, propinyloxy orbutinyloxy, represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine- methyl-, ethyl-, n- or i-propyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyloxy, phenylthio, phenylsulphinyl,phenylsulphonyl, phenylcarbonyloxy, phenylcarbonylmethoxy,phenylsulphonyloxy, phenylmethoxy, phenylmethylthio,phenylmethylsulphinyl or phenylmethylsulphonyl.

[0069] R⁵ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, represents in each case optionally fluorine- and/orchlorine-substituted methyl, ethyl, n- or i-propyl, methoxy, ethoxy, n-or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or representsin each case optionally cyano-, fluorine-, chlorine- ormethyl-substituted cyclopropyl.

[0070] R⁶ very particularly preferably represents hydrogen, representsin each case optionally cyano-, fluorine-, chlorine-, methoxy orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally fluorine- or chlorine-substitutedpropenyl, butenyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, or represents in each caseoptionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl or phenylmethyl.

[0071] R⁷ very particularly preferably represents hydroxyl, representsformyloxy, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methoxy,ethoxy, n- or i-propoxy, acetyloxy, propionyloxy, n- or i-butyroyloxy,methoxycarbonyloxy, ethoxycarbonyloxy, n- or i-propoxycarbonyloxy,methylaminocarbonyloxy, ethylaminocarbonyloxy, n- ori-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n- ori-propylsulphonyloxy, represents in each case optionally fluorine-and/or chlorine-substituted propenyloxy, butenyloxy, propinyloxy orbutinyloxy, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy, difluoromethoxy-or trifluoromethoxy-substituted phenylmethoxy, phenylcarbonyloxy,phenylcarbonylmethoxy or phenylsulphonyloxy.

[0072] R⁸ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, or represents in each case optionallyfluorine-, chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n-or i-propyl, acetyl, propionyl, n- or i-butyroyl, methoxy, ethoxy, n- ori-propoxy, methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl,methylthio, ethylthio, n- or i-propylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl or ethylsulphonyl.

[0073] R⁹ very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or representsoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl.

[0074] R¹⁰ very particularly preferably represents hydrogen, representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or representsoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl.

[0075] R¹¹ very particularly preferably represents hydrogen, cyano,fluorine, chlorine, bromine, or represents in each case optionallyfluorine-, chlorine-, methoxy-, or ethoxy-substituted methyl, ethyl, n-or i-propyl, methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl,ethoxy-carbonyl, n- or i-propoxycarbonyl, methylthio, ethylthio, n- ori-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl orethylsulphonyl.

[0076] R¹ most preferably represents hydrogen, or represents in eachcase optionally fluorine-, chlorine-, methoxy- or ethoxy-substitutedmethyl, ethyl, n- or i-propyl, represents methoxy or ethoxy orrepresents the grouping —C(Q)-R².

[0077] R² most preferably represents hydrogen, amino, hydrazino, orrepresents in each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl or n- or i-propyl, representsmethylamino, ethylamino, n- or i-propylamino or dimethylamino,represents in each case optionally fluorine-, chlorine- ormethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,represents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine- methyl-, ethyl- or n- or i-propyl-, methoxy-, ethoxy-, n- ori-propoxy-substituted phenyl, phenylamino, phenylmethyl or phenylethyl,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl, difluoromethyl-, trifluoromethyl-,dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-,fluorodichloromethyl-, methoxy-, ethoxy-, methylthio-, ethylthio-,difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl- orethoxycarbonyl-substituted furyl, furylmethyl, thienyl, thienylmethyl,pyrrolyl or pyrrolylmethyl.

[0078] X most preferably represents hydrogen, nitro, fluorine, chlorine,bromine, methyl, ethyl or trifluoromethyl.

[0079] Y most preferably represents hydrogen, nitro, cyano, fluorine,chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl.

[0080] R³ most preferably represents hydrogen or in each case optionallyfluorine- and/or chlorine-substituted methyl or ethyl.

[0081] R⁴ most preferably represents hydroxyl.

[0082] R⁵ most preferably represents hydrogen, fluorine, chlorine orrepresents in each case optionally fluorine- and/or chlorine-substitutedmethyl, ethyl, methoxy or ethoxy.

[0083] R⁶ most preferably represents hydrogen or represents in each caseoptionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,ethyl, n- or i-propyl or n-, i-, s- or t-butyl.

[0084] R⁷ most preferably represents hydroxyl, or represents in eachcase optionally fluorine-, or chlorine-substituted methoxy or ethoxy, orrepresents optionally nitro-, cyano-, fluorine-, chlorine-, bromine,methyl-, ethyl-, trifluoromethyl-, methoxy- or ethoxy-substitutedphenylmethoxy.

[0085] Preference according to the invention is given to the compoundsof the formula (I) which contain a combination of the meanings givenabove as being preferred.

[0086] Particular preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being particularly preferred.

[0087] Very particular preference according to the invention is given tothe compounds of the formula (I) which contain a combination of themeanings given above as being very particularly preferred.

[0088] Most preference according to the invention is given to thecompounds of the formula (I) which contain a combination of the meaningsgiven above as being most preferred.

[0089] Particular emphasis is given to the compounds of the formulae(I-1) to (I-3):

[0090] Here, the A¹, A², Q, R¹, R², X, Y and Z each have the meaningsgiven above as being preferred or being very particularly preferred.

[0091] Particular emphasis is furthermore given to the compounds of thegeneral formulae (I-2A) to (I-2D):

[0092] Here, m, A¹, A², Q, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹,X and Y each have the meanings given above as being preferred or asbeing very particularly preferred.

[0093] Among the compounds of the formulae (I-1) to (I-3) and (I-2A) to(I-2D), very particular emphasis is given to those in which A¹represents a single bond and A² represents methylene.

[0094] Among the compounds of the formulae (I-1) to (I-3) and (I-2A) to(I-2D), very particular emphasis is furthermore also given to those inwhich A¹ represents O (oxygen) and A² represents ethane-1,2-diyl(dimethylene).

[0095] The general or preferred radical definitions given above applyboth to the end products of the formula (I) and, correspondingly, to thestarting materials or intermediates required in each case for thepreparation. These radical definitions can be combined with one anotheras desired, i.e. including combinations between the given preferredranges.

[0096] The novel substituted aryl ketones of the formula (I) have strongand selective herbicidal activity.

[0097] The novel substituted aryl ketones of the formula (I) areobtained when

[0098] (a) amino compounds of the general formula (II)

[0099] in which

[0100] A¹, A², R¹, X, Y and Z are as defined above.

[0101] are reacted with compounds of the general formula (III)

[0102] in which

[0103] Q and R² are as defined above and

[0104] Q¹ represents halogen, alkoxy, alkylthio, aryloxy or arylthio,preferably represents chlorine, bromine, methoxy, ethoxy, methylthio,ethylthio, phenyloxy or phenylthio,

[0105] or, if appropriate, with corresponding iso(thio)cyanates

[0106] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,

[0107] or when

[0108] (b) carboxylic acids of the general formula (IV)

[0109] in which

[0110] A¹, A², Q, R¹, R², X and Y are as defined above,

[0111] or reactive derivatives thereof, such as, for example,corresponding acid halides, acid cyanides or esters

[0112] are reacted with compounds of the general formula (V)

H-Z   (V)

[0113] in which

[0114] Z is as defined above,

[0115] if appropriate in the presence of a dehydrating agent and also,if appropriate in the presence of one or more reaction auxiliaries and,if appropriate, in the presence of one or more diluents,

[0116] or when

[0117] (c) substituted benzoyl ketones of the general formula (Ia)

[0118] in which

[0119] A¹, A², Q, R¹, R², R¹⁰, X and Y are as defined above,

[0120] are reacted with an orthoformic ester or with aN,N-dimethyl-formamide acetal or with a cyanoformic ester or with carbondisulphide and an alkylating agent and subsequently with hydroxylamineor an acid adduct thereof,

[0121] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,

[0122] or when

[0123] (d) aryl ketones of the general formula (VI)

[0124] in which

[0125] A¹, A², Q, R¹, X, Y and Z are as defined above and

[0126] Q² represents halogen, alkoxy, alkylthio, aryloxy or arylthio,preferably represents chlorine, bromine, methoxy, ethoxy, methylthio,ethylthio, phenyloxy or phenylthio,

[0127] or, if appropriate, corresponding iso(thio)cyanates

[0128] are reacted with compounds of the general formula (VII)

H—R²   (VII)

[0129] in which

[0130] R² is as defined above,

[0131] if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,

[0132] and following the practice of the process (a), (b), (c) or (d)according to the invention, the resulting compounds of the generalformula (I) are, if appropriate and within the bounds of the definitionof substituents, subjected to subsequent reactions (for example,substition, oxidation or reduction reactions) according to customarymethods for conversion into other compounds of the general formula (I).

[0133] Using, for example,[3-(2-amino-ethoxy)-2-chloro-4-methylthio-phenyl]-(5-ethyl-4-isoxazolyl)-isoxazolyl)-methanoneand propionyl chloride as starting materials, the course of the reactionin the process (a) according to the invention can be illustrated by thefollowing equation:

[0134] Using, for example,4-bromo-3-[[(1-pyrrolidinylthioxomethyl)-amino]-methyl]-benzoic acid andcyclohexane-1,3-dione as starting materials, the course of the reactionin the process (b) according to the invention can be illustrated by thefollowing equation:

[0135] Using, for example,N-[2-chloro-5-(3-cyclopropyl-3-oxo-propanoyl)-benzyl]-acetamide,N,N-dimethyl-formamide diethyl acetal and hydroxylamine as startingmaterials, the course of the reaction in the process (c) according tothe invention can be illustrated by the following equation:

[0136] Using, for example, O-methylN-[[2-bromo-5-[(5-hydroxy-1-methyl-1H-pyrazol-4-yl)-carbonyl]-phenyl]-methyl]-carbamateand pyrrolidine as starting materials, the course of the reaction of theprocess (d) according to the invention can be illustrated by thefollowing equation:

[0137] The formula (II) provides a general definition of the aminocompounds to be used as starting materials in the process (a) accordingto the invention for preparing compounds of the general formula (I). Inthe general formula (II), A¹, A², R¹, X, Y and Z preferably have thosemeanings which have already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for A¹, A², R¹, X, Y and Z.

[0138] The starting materials of the general formula (II) have hithertonot been disclosed in the literature; as novel substances, they alsoform part of the subject-matter of the present application.

[0139] The novel amino compounds of the general formula (II) areobtained when halogen compounds of the general formula (VIII)

[0140] in which

[0141] A¹, A², X, Y and Z are as defined above and

[0142] X¹ represents halogen (preferably fluorine, chlorine, bromine oriodine, in particular chlorine or bromine),

[0143] are reacted with ammonia or amino compounds of the generalformula (IX)

[0144] in which

[0145] R¹ is as defined above,

[0146] if appropriate in the presence of a diluent, such as, forexample, tetrahydrofuran, and if appropriate under elevated pressure, attemperatures between 0° C. and 100° C. (cf. the Preparation Examples).

[0147] The intermediates of the general formula (VIII) are known and/orcan be prepared by processes known per se (cf. WO-A-95/3 1446,WO-A-00/68227, Preparation Examples).

[0148] The intermediates of the general formula (IX) are known chemicalsfor synthesis.

[0149] The formula (III) provides a general definition of the (thi)oxocompounds further to be used as starting materials in the process (a)according to the invention for preparing compounds of the generalformula (I). In the general formula (III), Q and R³ preferably havethose meanings which have already been given above, in connection withthe description of the compounds of the general formula (I) according tothe invention, as being preferred, particularly preferred, veryparticularly preferred or most preferred for Q and R³; Q¹ preferablyrepresents fluorine, chlorine, bromine, C₁-C₄-alkoxy, C₁-C₄-alkylthio,phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy orphenoxy.

[0150] The starting materials of the general formula (III) are knownorganic chemicals for synthesis.

[0151] The formula (IV) provides a general definition of the carboxylicacids to be used as starting materials in the process (b) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (IV), A¹, A², Q, R¹, R², X and Y preferably have thosemeanings which have already been given above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for A¹, A², Q, R¹, R², X and Y.

[0152] The starting materials of the general formula (IV) have hithertonot been disclosed in the literature; as novel substances, they alsoform part of the subject-matter of the present application.

[0153] The novel carboxylic acids of the general formula (IV) areobtained when

[0154] (α) iso(thio)cyanates of the general formula (X)

[0155] in which

[0156] A¹, A², Q, X and Y are as defined above and

[0157] R represents hydrogen, an alkali metal or an alkaline earth metalequivalent (preferably sodium or potassium) or alkyl (preferablyC₁-C₄-alkyl, in particular methyl or ethyl),

[0158] are reacted with compounds of the general formula (VII)

H—R²   (VII)

[0159] in which

[0160] R² is as defined above,

[0161] if appropriate in the presence of a diluent, such as, forexample, acetonitrile or ethanol, at temperatures between 0° C. and 100°C., followed, if appropriate, by an ester hydrolysis using customarymethods (cf. the Preparation Examples),

[0162] or when

[0163] (β) amino compounds of the general formula (XI)

[0164] in which

[0165] A¹, A², R¹, X and Y are as defined above and

[0166] R represents hydrogen, an alkali metal or an alkaline earth metalequivalent (preferably sodium or potassium) or alkyl (preferablyC₁-C₄-alkyl, in particular methyl or ethyl),

[0167] are reacted with (thi)oxo compounds of the general formula (III)

[0168] in which

[0169] Q and R² are as defined above and

[0170] Q¹ represents halogen, alkoxy, alkylthio, aryloxy or arylthio,preferably chlorine, bromine, methoxy, ethoxy, methylthio, ethylthio,phenyloxy or phenylthio,

[0171] or, if appropriate, with corresponding iso(thio)cyanates

[0172] if appropriate in the presence of one or more reactionauxiliaries, such as, for example, potassium carbonate or triethylamine,and if appropriate in the presence of one or more diluents, such as, forexample, acetonitrile or N,N-dimethyl-formamide, at temperatures between0° C. and 100° C.

[0173] The formula (V) provides a general definition of the compoundsfurther to be used as starting materials in the process (b) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (V), Z preferably has that meaning which has alreadybeen given above, in connection with the description of the compounds ofthe general formula (I) according to the invention, as being preferred,particularly preferred, very particularly preferred or most preferredfor Z.

[0174] The starting materials of the general formula (V) are knownorganic chemicals for synthesis.

[0175] The formula (Ia) provides a general definition of the substitutedbenzoyl ketones to be used as starting materials in the process (c)according to the invention for preparing compounds of the generalformula (I). In the general formula (Ia), A¹, A², Q, R¹, R², R¹⁰, X andY preferably have those meanings which have already been mentionedabove, in connection with the description of the compounds of thegeneral formula (I) according to the invention, as being preferred,particularly preferred, very particularly preferred or most preferredfor A¹, A², Q, R¹, R², R¹⁰, X and Y.

[0176] As novel substances, the starting materials of the generalformula (Ia) also form part of the subject-matter of the presentapplication; they can be prepared by the process (a) or (b) according tothe invention.

[0177] The formula (VI) provides a general definition of the arylketones to be used as starting materials in the process (d) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (VI), A¹, A², Q, R¹, X, Y and Z preferably have thosemeanings which have already been mentioned above, in connection with thedescription of the compounds of the general formula (I) according to theinvention, as being preferred, particularly preferred, very particularlypreferred or most preferred for A¹, A², Q, R¹, X, Y and Z; Q² preferablyrepresents fluorine, chlorine, bromine, C₁-C₃-alkoxy, C₁-C₃-alkylthio,phenoxy or phenylthio, in particular chlorine, methoxy, ethoxy orphenoxy.

[0178] The starting materials of the formula (VI) can be prepared byprocesses known to the person skilled in the art.

[0179] The formula (VII) provides a general definition of the compoundsfurther to be used as starting materials in the process (d) according tothe invention for preparing compounds of the general formula (I). In thegeneral formula (VII), R² preferably has that meaning which has alreadybeen mentioned above, in connection with the description of the generalformula (I), as being preferred, particularly preferred, veryparticularly preferred or most preferred for R².

[0180] The starting materials of the general formula (VII) are knownorganic compounds.

[0181] The formula (X) provides a general definition of theiso(thio)cyanates to be used as starting materials in the process (cc)according to the invention for preparing compounds of the generalformula (IV). In the general formula (X), A¹, A², Q, X and Y preferablyhave that meaning which has already been mentioned above, in connectionwith the description of the general formula (I), as being preferred,particularly preferred, very particularly preferred or most preferredfor A¹, A², Q, X and Y.

[0182] The starting materials of the general formula (X) can be obtainedby processes known to the person skilled in the art.

[0183] The formula (XI) provides a general definition of the aminocompounds to be used as starting materials in the process (p) accordingto the invention for preparing compounds of the general formula (IV). Inthe general formula (XI), A¹, A², R¹, X and Y preferably have thatmeaning which has already been mentioned above, in connection with thedescription of the general formula (I), as being preferred, particularlypreferred, very particularly preferred or most preferred for A¹, A², R¹,X and Y.

[0184] The starting materials of the general formula (XI) can beprepared by processes known to the person skilled in the art.

[0185] The process (a), (b), (c) and (d) according to the invention arepreferably carried out using one or more reaction auxiliaries. Suitablereaction auxiliaries for the processes (a), (b), (c) and (d) accordingto the invention are, in general, the customary inorganic or organicbases or acid acceptors. These preferably include alkali metal oralkaline earth metal acetates, amides, carbonates, bicarbonates,hydrides, hydroxides or alkoxides, such as, for example, sodium acetate,potassium acetate, or calcium acetate, lithium amide, sodium amide,potassium amide or calcium amide, sodium carbonate, potassium carbonateor calcium carbonate, sodium bicarbonate, potassium bicarbonate orcalcium bicarbonate, lithium hydride, sodium hydride, potassium hydrideor calcium hydride, lithium hydroxide, sodium hydroxide, potassiumhydroxide or calcium hydroxide, sodium methoxide, ethoxide, n- ori-propoxide, n-, i-, s- or t-butoxide or potassium methoxide, ethoxide,n- or i-propoxide, n-, i-, s- or t-butoxide; furthermore also basicorganic nitrogen compounds, such as, for example, trimethylamine,triethylamine, tripropylamine, tributylamine, ethyl-diisopropylamine,N,N-dimethyl-cyclohexylamine, dicyclohexylamine,ethyl-dicyclohexylamine, N,N-dimethyl-aniline, N,N-dimethyl-benzylamine,pyridine, 2-methyl-, 3-methyl-, 4-methyl-, 2,4-dimethyl-, 2,6-dimethyl-,3,4-dimethyl- and 3,5-dimethylpyridine, 5-ethyl-2-methyl-pyridine,4-dimethylamino-pyridine, N-methyl-piperidine, N-ethyl-piperidine,N-methyl-morpholine, N-ethyl-morpholine, 1,4-diaza-bicyclo[2.2.2]-octane(DABCO), 1,5-diazabicyclo[4.3.0]-non-5-ene (DBN), or1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU).

[0186] Further reaction auxiliaries suitable for the processes (a), (b),(c) and (d) according to the invention are phase-transfer catalysts.Examples of such catalysts which may be mentioned are:

[0187] Tetrabutylammonium bromide, tetrabutylammonium chloride,tetraoctylammonium chloride, tetrabutylammonium hydrogensulphate,methyl-trioctylammonium chloride, hexadecyl-trimethylammonium chloride,hexadecyl-triethylammonium bromide, benzyl-trimethylammonium chloride,benzyl-triethylammonium chloride, benzyl-trimethylammonium hydroxide,benzyl-triethylammonium hydroxide, benzyltributylammonium chloride,benzyl-tributylammonium bromide, tetrabutylphosphonium bromide,tetrabutylphosphonium chloride, tributyl-hexadecylphosphonium bromide,butyl-triphenylphosphonium chloride, ethyl-trioctylphosphonium bromide,tetra-phenylphosphonium bromide.

[0188] The process (b) according to the invention for preparing thenovel substituted aryl ketones of the general formula (I) is, ifappropriate, carried out using a dehydrating agent. Here, suitabledehydrating agents are the chemicals customarily suitable for bindingwater.

[0189] Examples which may be mentioned are dicyclohexylcarbodiimide,carbonyl-bisimidazole and propanephosphonic anhydride.

[0190] Dehydrating agents which may be mentioned as being particularlysuitable are dicyclohexcylcarbodimide and propanephosphonic anhydride.

[0191] The processes according to the invention for preparing thecompounds of the general formula (I) are preferably carried out usingdiluents. Suitable diluents for carrying out the processes (a), (b), (c)and (d) according to the invention are, in addition to water, especiallyinert organic solvents. These include, in particular, aliphatic,alicyclic or aromatic, optionally halogenated hydrocarbons, such as, forexample, benzine, benzene, toluene, xylene, chlorobenzene,dichlorobenzene, petroleum ether, hexane, cyclohexane, dichloromethane,chloroform, carbon tetrachloride; ethers, such as diethyl ether,diisopropyl ether, dioxane, tetrahydrofuran or ethylene glycol dimethylether or ethylene glycol diethyl ether, ketones, such as acetone,butanone or methyl isobutyl ketone; nitriles, such as acetonitrile,propionitrile or butyronitrile; amides, such as N,N-dimethylformamide,N,N-dimethylacetamide, N-methyl-formanilide, N-methyl-pyrrolidone orhexamethylphosphoric triamide; esters, such as methyl acetate or ethylacetate; sulphoxides, such as dimethyl sufoxide; alcohols, such asmethanol, ethanol, n- or i-propanol, ethylene glycol monomethyl ether,ethylene glycol monoethyl ether, diethylene glycol monomethyl ether,diethylene-glycol monoethyl ether, mixtures thereof with water or purewater.

[0192] When carrying out the processes (a), (b), (c) and (d) accordingto the invention, the reaction temperatures can be varied within arelatively wide range. In general, the processes are carried out attemperatures between 0° C. and 150° C., preferably between 10° C. and120° C.

[0193] The process according to the invention is generally carried outunder atmospheric pressure. However, it is also possible to carry outthe processes according to the invention under elevated or reducedpressure—in general between 0.1 bar and 10 bar.

[0194] For carrying out the processes according to the invention, thestarting materials are generally employed in approximately equimolaramounts. However, it is also possible to use a relatively large excessof one of the components. The reaction is generally carried out in asuitable diluent in the presence of a reaction auxiliary, and thereaction mixture is generally stirred at the required temperature forseveral hours. Work-up is carried out by customary methods (cf. thePreparation Examples).

[0195] The active compounds according to the invention can be used asdefoliants, desiccants, haulm killers and, especially, as weed killers.Weeds in the broadest sense are understood to mean all plants which growin locations where they are undesired. Whether the substances accordingto the invention act as total or selective herbicides dependsessentially on the amount used.

[0196] The active compounds according to the invention can be used, forexample, in connection with the following plants:

[0197] Dicotyledonous weeds of the genera: Abutilon, Amaranthus,Ambrosia, Anoda, Anthemis, Aphanes, Atriplex, Bellis, Bidens, Capsella,Carduus, Cassia, Centaurea, Chenopodium, Cirsium, Convolvulus, Datura,Desmodium, Emex, Erysimum, Euphorbia, Galeopsis, Galinsoga, Galium,Hibiscus, Ipomoea, Kochia, Lamium, Lepidium, Lindernia, Matricaria,Mentha, Mercurialis, Mullugo, Myosotis, Papaver, Pharbitis, Plantago,Polygonum, Portulaca, Ranunculus, Raphanus, Rorippa, Rotala, Rumex,Salsola, Senecio, Sesbania, Sida, Sinapis, Solanum, Sonchus, Sphenoclea,Stellaria, Taraxacum, Thlaspi, Trifolium, Urtica, Veronica, Viola,Xanthium.

[0198] Dicotyledonous crops of the genera: Arachis, Beta, Brassica,Cucumis, Cucurbita, Helianthus, Daucus, Glycine, Gossypium, Ipomoea,Lactuca, Linum, Lycopersicon, Nicotiana, Phaseolus, Pisum, Solanum,Vicia.

[0199] Monocotyledonous weeds of the genera: Aegilops, Agropyron,Agrostis, Alopecurus, Apera, Avena, Brachiaria, Bromus, Cenchrus,Commelina, Cynodon, Cyperus, Dactyloctenium, Digitaria, Echinochloa,Eleocharis, Eleusine, Eragrostis, Eriochloa, Festuca, Fimbristylis,Heteranthera, Imperata, Ischaemum, Leptochloa, Lolium, Monochoria,Panicum, Paspalum, Phalaris, Phleum, Poa, Rottboellia, Sagittaria,Scirpus, Setaria, Sorghum.

[0200] Monocotyledonous crops of the genera: Allium, Ananas, Asparagus,Avena, Hordeum, Oryza, Panicum, Saccharum, Secale, Sorghum, Triticale,Triticum, Zea.

[0201] However, the use of the active compounds according to theinvention is in no way restricted to these genera, but also extends inthe same manner to other plants.

[0202] The active compounds according to the invention are suitable,depending on the concentration, for the total control of weeds, forexample on industrial terrain and rail tracks, and on paths and areaswith and without tree plantings. Similarly, the active compoundsaccording to the invention can be employed for controlling weeds inperennial crops, for example forests, decorative tree plantings,orchards, vineyards, citrus groves, nut orchards, banana plantations,coffee plantations, tea plantations, rubber plantations, oil palmplantations, cocoa plantations, soft fruit plantings and hop fields, onlawns, turf and pastureland, and for the selective control of weeds inannual crops.

[0203] The compounds of the formula (I) according to the invention havestrong herbicidal activity and a broad active spectrum when used on thesoil and on above-ground parts of plants. To a certain extent they arealso suitable for the selective control of monocotyledonous anddicotyledonous weeds in monocotyledonous and dicotyledonous crops, bothby the pre-emergence and by the post-emergence method.

[0204] At certain concentrations or application rates, the activecompounds according to the invention can also be employed forcontrolling animal pests and fungal or bacterial plant diseases. Ifappropriate, they can also be used as intermediates or precursors forthe synthesis of other active compounds.

[0205] All plants and plant parts can be treated in accordance with theinvention. Plants are to be understood as meaning in the present contextall plants and plant populations such as desired and undesired wildplants or crop plants (including naturally occurring crop plants). Cropplants can be plants which can be obtained by conventional plantbreeding and optimization methods or by biotechnological and recombinantmethods or by combinations of these methods, including the transgenicplants and inclusive of the plant cultivars protectable or notprotectable by plant breeders' rights. Plant parts are to be understoodas meaning all parts and organs of plants above and below the ground,such as shoot, leaf, flower and root, examples which may be mentionedbeing leaves, needles, stalks, stems, flowers, fruit bodies, fruits,seeds, roots, tubers and rhizomes. The plant parts also includeharvested material, and vegetative and generative propagation material,for example cuttings, tubers, rhizomes, offsets and seeds.

[0206] As already mentioned above, it is possible to treat all plantsand their parts according to the invention. In a preferred embodiment,wild plants (weeds, harmful plants) and/or plant species and plantcultivars (crop plants) obtained by conventional biological breedingmethods, such as crossing or protoplast fusion, and parts thereof, aretreated. In a further preferred embodiment, transgenic plants and plantcultivars obtained by genetic engineering, if appropriate in combinationwith conventional methods (Genetically Modified Organisms), and partsthereof are treated. The term “parts” or “parts of plants” or “plantparts” has been explained above.

[0207] Plant cultivars are to be understood as meaning crop plantshaving certain properties (“traits”) which have been obtained byconventional breeding, by mutagenesis or by recombinant DNA techniques.They can be cultivars, bio- or genotypes.

[0208] The transgenic plants or plant cultivars (i.e. those obtained bygenetic engineering) which are treated according to the inventioninclude all plants which, in the genetic modification, received geneticmaterial which imparted particularly advantageous useful properties(“traits”) to these plants. Examples of such properties are better plantgrowth, increased tolerance to high or low temperatures, increasedtolerance to drought or to water or soil salt content, increasedflowering performance, easier harvesting, accelerated maturation, higherharvest yields, better quality and/or a higher nutritional value of theharvested products, better storage stability and/or processability ofthe harvested products. Further and particularly emphasized examples ofsuch properties are a better defence of the plants against animal andmicrobial pests, such as against insects, mites, phytopathogenic fungi,bacteria and/or viruses, and also increased tolerance of the plants tocertain herbicidally active compounds. Examples of transgenic plantswhich may be mentioned are the important crop plants, such as cereals(including rice), maize, soya beans, potatoes, cotton, beets, cultivatedgrasses such as golfing greens and ornamental lawns, oilseed rape, fruitplants (with the fruits apples, pears, citrus fruits and grapes), andplantation crops, such as oil and rubber trees, where particularemphasis is given to cereals including rice), maize, soya beans,potatoes, cotton, beets and oilseed rape. Traits that are emphasized arein particular increased defence of the plants against insects by toxinsformed in the plants, in particular those formed in the plants by thegenetic material from Bacillus thuringiensis (for example by the genesCryIA(a), CryIA(b), CryIA(c), CryIIA, CryIIA, CryIIIB2, Cry9c Cry2Ab,Cry3Bb and CryIF and also combinations thereof) (hereinbelow referred toas “Bt plants”). Traits that are also particularly emphasized are theincreased defence of the plants to fungi, bacteria and viruses bysystemic acquired resistance (SAR), systemin, phytoalexins, elicitorsand resistance genes and correspondingly expressed proteins and toxins.Traits that are furthermore particularly emphasized are the increasedtolerance of the plants to certain herbicidally active compounds andclasses of active compounds, such as glyphosate orglufosinate/phosphinotricin (for example the “PAT” gene), ALSinhibitors, such as imidazolinones, sulphonylureas and others, PPOinhibitors (for example plants having Acuron genes), 4-HPD inhibitors,such as isozazoles (for example isoxaflutole), ACCase inhibitors, suchas sethoxydim, and also bromoxynil.

[0209] The genes which impart the desired traits in question can also bepresent in combinations with one another in the transgenic plants.Examples of “Bt plants” which may be mentioned are maize cultivars,cotton cultivars, soya bean cultivars and potato cultivars which aresold under the trade names YIELD GARD® (for example maize, cotton, soyabeans), KnockOut® (for example maize), StarLink® (for example maize),Bollgard® (cotton), Nucotn® (cotton) and NewLeaf® (potato). Examples ofherbicide-tolerant plants which may be mentioned are maize cultivars,cotton cultivars, soya bean cultivars, cereal cultivars including ricecultivars, beet cultivars and oilseed rape cultivars which are soldunder the trade names Roundup Ready® (tolerance to glyphosate, forexample maize, cotton, soya bean, beets, oilseed rape), Liberty Link®(tolerance to glufosinate, for example oilseed rape, maize, beets), IMI®(tolerance to imidazolinones) and STS® (tolerance to sulphonylureas, forexample maize). Herbicide-resistant plants (plants bred in aconventional manner for herbicide tolerance) which may be mentionedinclude the cultivars sold under the name Clearfield® (for examplemaize, rice).

[0210] Of course, these statements also apply to plant cultivars havingthese genetic traits or genetic traits still to be developed, whichplants will be developed and/or marketed in the future.

[0211] Depending on the plant species or plant cultivars, their locationand growth conditions (soils, climate, vegetation period, diet), thetreatment according to the invention may also result in superadditive(“synergistic”) effects. Thus, for example, reduced application ratesand/or a widening of the activity spectrum and/or an increase in theactivity of the substances and compositions to be used according to theinvention—also in combination with other agrochemical active compounds—,better plant growth, increased tolerance to high or low temperatures,increased tolerance to drought or to water or soil salt content,increased flowering performance, easier harvesting, acceleratedmaturation, higher harvest yields, better quality and/or a highernutritional value of the harvested products, better storage stabilityand/or processability of the harvested products are possible whichexceed the effects which were actually to be expected.

[0212] The plants listed can be treated according to the invention in aparticularly advantageous manner with the compounds of the generalformula (I) or the active compound mixtures according to the inventionwhere in addition to the good control of weed plants, the abovementionedsynergistic effects with the transgenic plants or plant cultivars occur.The preferred ranges stated above for the active compounds or mixturesalso apply to the treatment of these plants. Particular emphasis isgiven to the treatment of plants with the compounds or mixturesspecifically mentioned in the present text.

[0213] The treatment according to the invention of the plants and plantparts with the active compounds is carried out directly or by allowingthe compounds to act on their surroundings, environment or storage spaceby the customary treatment methods, for example by immersion, spraying,evaporation, fogging, scattering, painting on and, in the case ofpropagation material, in particular in the case of seeds, also byapplying one or more coats.

[0214] The active compounds can be converted into the customaryformulations such as solutions, emulsions, wettable powders,suspensions, powders, dusts, pastes, soluble powders, granules,suspension-emulsion concentrates, natural and synthetic materialsimpregnated with active compound, and microencapsulations in polymericmaterials.

[0215] These formulations are produced in a known manner, for example bymixing the active compounds with extenders, that is, liquid solventsand/or solid carriers, optionally with the use of surfactants, that is,emulsifiers and/or dispersants, and/or foam formers.

[0216] If the extender used is water, it is also possible, for example,to use organic solvents as cosolvents. The following are essentiallysuitable as liquid solvents: aromatics such as xylene, toluene oralkylnaphthalenes, chlorinated aromatics or chlorinated aliphatichydrocarbons such as chlorobenzenes, chloroethylenes or methylenechloride, aliphatic hydrocarbons such as cyclohexane or paraffins, forexample mineral oil fractions, mineral and vegetable oils, alcohols suchas butanol or glycol and their ethers and esters, ketones such asacetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone,strongly polar solvents such as dimethylformamide and dimethylsulphoxide, or else water.

[0217] Suitable solid carriers are: for example ammonium salts andground natural minerals such as kaolins, clays, talc, chalk, quartz,attapulgite, montmorillonite or diatomaceous earth, and ground syntheticminerals such as highly-disperse silica, alumina and silicates; suitablesolid carriers for granules are: for example crushed and fractionatednatural rocks such as calcite, marble, pumice, sepiolite and dolomite,or else synthetic granules of inorganic and organic minerals, andgranules of organic material such as sawdust, coconut shells, maize cobsand tobacco stalks; suitable emulsifiers and/or foam formers are: forexample nonionic and anionic emulsifiers such as polyoxyethylene fattyacid esters, polyoxyethylene fatty alcohol ethers, for example alkylarylpolyglycol ethers, alkylsulphonates, alkyl sulphates, arylsulphonates,or else protein hydrolysates; suitable dispersants are: for examplelignin-sulphite waste liquors and methylcellulose.

[0218] Tackifiers such as carboxymethylcellulose and natural andsynthetic polymers in the form of powders, granules or latices, such asgum arabic, polyvinyl alcohol and polyvinyl acetate, or else naturalphospholipids such as cephalins and lecithins and syntheticphospholipids can be used in the formulations. Other additives can bemineral and vegetable oils.

[0219] It is possible to use colorants such as inorganic pigments, forexample iron oxide, titanium oxide and Prussian Blue, and organiccolorants such alizarin colorants, azo colorants and metalphthalocyanine colorants, and trace nutrients such as salts of iron,manganese, boron, copper, cobalt, molybdenum and zinc.

[0220] The formulations generally comprise between 0.1 and 95 per centby weight of active compound, preferably between 0.5 and 90%.

[0221] For controlling weeds, the active compounds according to theinvention, as such or in their formulations, can also be used asmixtures with known herbicides and/or substances which improve thecompatibility with crop plants (“safeners”), finished formulations ortank mixes being possible. Also possible are mixtures with weed-killerscomprising one or more known herbicides and a safener.

[0222] Suitable components for the mixtures are known herbicides, forexample acetochlor, acifluorfen (-sodium), aclonifen, alachlor,alloxydim (-sodium), ametryne, amicarbazone, amidochlor, amidosulfuron,amitrole, anilofos, asulam, atrazine, azafenidin, azimsulfuron,beflubutamid, benazolin (-ethyl), benfuresate, bensulfuiron (-methyl),bentazon, benzfendizone, benzobicyclon, benzofenap, benzoylprop(-ethyl), bialaphos, bifenox, bispyribac (-sodium), bromacil,bromobutide, bromofenoxim, bromoxynil, butachlor, butafenacil (-allyl),butenachlor, butralin, butroxydim, butylate, cafenstrole, carbetamide,carfentrazone (-ethyl), chlomethoxyfen, chloramben, chloridazon,chlorimuron (-ethyl), chlornitrofen, chlorsulfuron, chlorthiamid,chlortoluron, cinidon (-ethyl), cinmethylin, cinosulfuron, clefoxydim,clethodim, clodinafop (-propargyl), clomazone, clomeprop, clopyralid,cloransulam (-methyl), cumyluron, cyanazine, cybutryne, cycloate,cyclosulfamuron, cycloxydim, cyhalofop (-butyl), 2,4-D, 2,4-DB,desmedipham, diallate, dicamba, dichlobenil, dichlorprop (—P), diclofop(-methyl), diclosulam, diethatyl (-ethyl), difenopenten (-ethyl),difenzoquat, diflufenican, diflufenzopyr, dikegulac (-sodium),dimefuron, dimepiperate, dimethachlor, dimethametryn, dimethenamid,dimexyflam, dinitramine, diphenamid, diquat (-dibromide), dithiopyr,diuron, dymron, epropodan, EPTC, esprocarb, ethalfluralin,ethametsulfuron (-methyl), ethiozin, ethofumesate, ethoxyfen,ethoxysulfuron, etobenzanid, fenoxaprop (—P-ethyl), fentrazamide,flamprop (-M-isopropyl, -M-methyl), flazasulfuron, florasulam, fluazifop(-P-butyl), fluazolate, flucarbazone (-sodium), fluchloralin,flufenacet, flumetsulam, flumiclorac (-pentyl), flumioxazin,flumipropyn, fluometuron, fluorochloridone, fluoroglycofen (-ethyl),flupoxam, flupropacil, flurpyrsulfuron (-methyl, -sodium), flurenol(-butyl), fluridone, fluroxypyr (-butoxypropyl, -meptyl), flurprimidol,flurtamone, fluthiacet (-methyl), fomesafen, foramsulfuron, glufosinate(-ammonium), glyphosate (-ammonium, -isopropylammonium), halosafen,halosulfuron (-methyl), haloxyfop (-ethoxyethyl, -P-methyl), hexazinone,imazamethabenz (-methyl), imazamethapyr, imazamox, imazapic, imazapyr,imazaquin, imazethapyr, imazosulfuron, iodosulfuron (-methyl, -sodium),ioxynil, isopropalin, isoproturon, isouron, isoxaben, isoxachlortole,isoxadifen (-ethyl), isoxaflutole, isoxapyrifop, ketospiradox, lactofen,lenacil, linuron, MCPA, mecoprop (—P), mefenacet, mesotrione,metamitron, metazachlor, methabenzthiazuron, methyldymron, metobenzuron,metobromuron, (S-) metolachlor, metosulam, metoxuron, metribuzin,metsulfuron (-methyl), molinate, monolinuron, naproanilide, napropamide,neburon, nicosulfuron, norflurazon, orbencarb, oryzalin, oxadiargyl,oxadiazon, oxasulfuron, oxaziclomefone, oxyfluorfen, paraquat,pelargonic acid, pendimethalin, pendralin, pentoxazone, pethoxamid,phenmedipham, picolinafen, piperophos, pretilachlor, primisulfuron(-methyl), profluazol, profoxydim, prometryn, propachlor, propanil,propaquizafop, propisochlor, propoxycarbazone (-sodium), propyzamide,prosulfocarb, prosulfuron, pyraflufen (-ethyl), pyrazogyl, pyrazolate,pyrazosulfuron (-ethyl), pyrazoxyfen, pyribenzoxim, pyributicarb,pyridafol, pyridate, pyridatol, pyriftalid, pyriminobac (-methyl),pyrithiobac (-sodium), quinchlorac, quinmerac, quinoclamine, quizalofop(—P-ethyl, —P-tefuryl), rimsulfuron, sethoxydim, simazine, simetryn,sulcotrione, sulfentrazone, sulfometuron (-methyl), sulfosate,sulfosulfuron, tebutam, tebuthiuron, tepraloxydim, terbuthylazine,terbutryn, thenylchlor, thiazopyr, thidiazimin, thifensulfuron(-methyl), thiobencarb, tiocarbazil, tralkoxydim, triallate,triasulfuron, tribenuron (-methyl), triclopyr, tridiphane, trifluralin,trifloxysulfuron, triflusulfuron (-methyl), tritosulfuron.

[0223] Furthermore suitable for the mixtures are known safeners, forexample AD-67, BAS-145138, benoxacor, cloquintocet (-mexyl),cyometrinil, 2,4-D, DKA-24, dichlormid, dymron, fenclorim, fenchlorazol(-ethyl), flurazole, fluxofenim, furilazole, isoxadifen (-ethyl), MCPA,mecoprop (—P), mefenpyr (-diethyl), MG-191, oxabetrinil, PPG-1292,R-29148.

[0224] A mixture with other known active compounds, such as fungicides,insecticides, acaricides, nematicides, bird repellents, plant nutrientsand agents which improve soil structure, is also possible.

[0225] The active compounds can be used as such, in the form of theirformulations or in the use forms prepared therefrom by further dilution,such as ready-to-use solutions, suspensions, emulsions, powders, pastesand granules. They are used in a customary manner, for example bywatering, spraying, atomizing or broadcasting.

[0226] The active compounds according to the invention can be appliedboth before and after emergence of the plants. They can also beincorporated into the soil before sowing.

[0227] The amount of active compound used can vary within a relativelywide range. It depends essentially on the nature of the desired effect.In general, the amounts used are between 1 g and 10 kg of activecompound per hectare of soil surface, preferably between 5 g and 5 kgper ha.

[0228] The preparation and the use of the active compounds according tothe invention is illustrated by the examples below.

PREPARATION EXAMPLES Example 1

[0229]

[0230] (Process (a))

[0231] 0.28 g (3.6 mmol) of acetyl chloride is added to a suspension of1.0 g (2.9 mmol) of[3-(2-aminoethoxy)-2,4-dichloro-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanoneand 0.8 g (5.8 mmol) of potassium carbonate in 6 ml of acetonitrile, andthe reaction mixture is stirred at room temperature (about 20° C.) for24 hours. The solvent is then removed under reduced pressure and theresidue is dissolved in a little water. The aqueous solution is washedwith dichloromethane and then acidified with conc. hydrochloric acid andextracted with ethyl acetate. The organic phase is washed with saturatedaqueous sodium chloride solution, dried over sodium sulphate andfiltered. From the filtrate, the solvent is carefully distilled offunder reduced pressure.

[0232] This gives 0.8 g (71.5% of theory) ofN-(2-{2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-acetamide(Example I-2-1) as an orange-yellow glass-like solid.

[0233] log P=1.41.

Example 2

[0234]

[0235] (Process (a))

[0236] 0.24 g (3.3 mmol) of methyl isothiocyanate is added to asuspension of 0.5 g (1.45 mmol) of[3-(2-amino-ethoxy)-2,4-dichloro-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanonein 10 ml of methanol, and the reaction mixture is heated at the boilunder reflux for 24 hours. Water and ethyl acetate are added and theorganic phase is then separated off, washed with saturated aqueoussodium chloride solution, dried over sodium sulphate and filtered. Fromthe filtrate, the solvent is carefully distilled off under reducedpressure.

[0237] This gives 0.55 g (91% of theory) ofN-(2-{2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-N′-methyl-thiourea(Example I-2-2) as an orange-yellow viscous oil.

[0238] log P=1.60.

Example 3

[0239]

[0240] (Process (b))

[0241] 0.7 g (6.25 mmol) of 1,3-cyclohexanedione and 2.0 g (6.25 mmol)of N-(3-carboxyl-2,6-dichloro-benzyl)-N′-isopropyl-thiourea areinitially charged to 50 ml of acetonitrile. 1.5 g (7.25 mmol) ofdicyclohexylcarbodiimide are added and the mixture is stirred at roomtemperature (about 20° C.) for 15 hours. 0.7 g (7 mmol) of triethylamineand 0.7 g (8 mmol) of 2-hydroxy-2-methyl-propionitrile is then added,and the mixture is stirred at room temperature for another 15 hours. Themixture is then stirred with 50 ml of aqueous 1M potassium carbonatesolution and filtered off with suction, and the filtrate is acidified topH 4 using hydrochloric acid. The mixture is extracted three times within each case 30 ml of dichloromethane and the combined organic phasesare dried with magnesium sulphate and filtered. The solvent is thenremoved under reduced pressure.

[0242] This gives 1.1 g (30% of theory) ofN-(3-(cyclohex-1-en-2-ol-6-on-1-ylcarbonyl)-2,4-dichlorobenzyl)-N′-isopropyl-thiourea(Example I-2-3) as an oily residue.

[0243] log P=2.74.

Example 4

[0244]

[0245] (Subsequent Reaction)

[0246] 0.25 g (1.0 mmol) of 1-bromo-4-(bromomethyl)-benzene and 0.15 gof 1,8-diazabicyclo-(5.4.0)-undec-7-en (DBU) are added to a solution of0.193 g (0.5 mmol) ofN-(2-{2,6-dichloro-3-[(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-carbonyl]-phenoxy}-ethyl)-acetamidein 6 ml of toluene, and the reaction mixture is heated at the boil underreflux for 9 hours. The supernatant toluene phase is decanted off andthe oily residue that remains is separated by column chromatographyusing the mobile phase dichloromethane/methanol (9:1).

[0247] This gives 0.12 g (43% of theory) ofN-{2-[3-({5-[(4-bromo-benzyl)-oxy]-1-ethyl-1H-pyrazol-4-yl}-carbonyl)-2,6-dichloro-phenoxy]-ethyl}-acetamide(Example I-2-4) as a yellow viscous oil.

[0248] log P=2.06.

[0249] Analogously to Examples 1 to 4 and in accordance with the generaldescription of the preparation processes according to the invention, itis also possible to prepare, for example, the compounds of the generalformula (I)—or of the formulae (I-1) to (I-3) or the formulae (I-2a) to(I-2d)—listed in Table 1 below.

TABLE 1 Examples of compounds of the formula (I-2) (I-2)

(position) (position) Physical Ex. No. A¹ A² Q R¹ R² X Y Z data I-2-5 O(CH₂)₂ O H

(2) Cl (4) Cl

log P = 1.64^(a)) I-2-6 O (CH₂)₂ O H

(2) Cl (4) Cl

log P = 1.78^(a)) I-2-7 O (CH₂)₂ O H

(2) Cl (4) Cl

log P = 2.63^(a)) I-2-8 O (CH₂)₂ O

(2) Cl (4) Cl

I-2-9 — CH₂ S H

(2) Cl (4) Cl

log P = 3.05^(a)) I-2-10 — CH₂ O C₃H₇-i

(2) Cl (4) Cl

log P = 2.86^(a)) I-2-11 — CH₂ O C₃H₇-i

(2) Cl (4) Cl

log P 2.02^(a)) I-2-12 — CH₂ O C₃H₇-i NH₂ (2) Cl (4) Cl

log P = 2.03^(a)) I-2-13 O (CH₂)₂ O H

(2) Cl (4) Cl

log P = 2.12^(a)) I-2-14 — CH₂ O C₃H₇-i NH₂ (2) Cl (4) Cl

log P = 1.32^(a)) I-2-15 — CH₂ O C₃H₇-i

(2) Cl (4) Cl

log P = 2.33^(a)) I-2-16 — CH₂ O C₃H₇-i

(2) Cl (4) Cl

log P = 1.42^(a)) I-2-17 — CH₂ O C₃H₇-i N(CH₃)₂ (2) Cl (4) Cl

log P = 2.82^(a)) I-2-18 — CH₂ O C₃H₇-i N(CH₃)₂ (2) Cl (4) Cl

log P = 2.00^(a)) I-2-19 — CH₂ O H

(2) Cl (4) Cl

log P = 1.95^(a)) I-2-20 — CH₂ O H

(2) Cl (4) Cl

I-2-21 — CH₂ O H N(CH₃)₂ (2) Cl (4) Cl

log P = 1.87^(a)) I-2-22 — CH₂ O H

(2) Cl (4) Cl

log P = 1.35^(a)) I-2-23 — CH₂ O H N(CH₃)₂ (2) Cl (4) Cl

log P = 1.13^(a)) I-2-24 — CH₂ O

N(CH₃)₂ (2) Cl (4) Cl

log P = 2.45^(a)) I-2-25 — CH₂ O

N(CH₃)₂ (2) Cl (4) Cl

log P = 1.69^(a)) I-2-26 — CH₂ O

(2) Cl (4) Cl

I-2-27 — CH₂ O

(2) Cl (4) Cl

I-2-28 — CH₂ O

(2) Cl (4) Cl

I-2-29 — CH₂ O

(2) Cl (4) Cl

I-2-30 — CH₂ O H

(2) Cl (4) Cl

I-2-31 — CH₂ O H

(2) (4) Cl

I-2-32 — CH₂ O H

(2) Cl (4) Cl

I-2-33 — CH₂ O H

(2) Cl (4) Cl

I-2-34 — CH₂ O H

(2) Cl (4) Cl

I-2-35 — CH₂ O H

(2) Cl (4) Cl

I-2-36 — CH₂ O H

(2) Cl (4) Cl

I-2-37 — CH₂ O H

(2) Cl (4) Cl

I-2-38 — CH₂ O CH₃ NH₂ (2) Cl (4) Cl

I-2-39 — CH₂ O CH₃ NH₂ (2) Cl (4) Cl

I-2-40 — CH₂ O H NH₂ (2) Cl (4) Cl

I-2-41 — CH₂ O H NH₂ (2) Cl (4) Cl

I-2-42 — CH₂ O C₃H₇-i

(2) Cl (4) Cl

log P = 4.25^(a)) I-2-43 — CH₂ O C₃H₇-i

(2) Cl (4) Cl

log P = 3.19^(a)) I-2-44 — CH₂ O C₃H₇-i OC₂H₅ (2) Cl (4) Cl

log P = 3.69^(a)) I-2-45 — CH₂ O C₃H₇-i OC₂H₅ (2) Cl (4) Cl

log P = 2.69^(a)) I-2-46 — CH₂ O H OC₂H₅ (2) Cl (4) Cl

I-2-47 — CH₂ O H OC₂H₅ (2) Cl (4) Cl

I-2-48 — CH₂ O H OC₃H₇-i (2) Cl (4) Cl

I-2-49 — CH₂ O H OC₃H₇-i (2) Cl (4) Cl

I-2-50 — CH₂ O CH₃ OC₂H₅ (2) Cl (4) Cl

I-2-51 — CH₂ O CH₃ OC₂H₅ (2) Cl (4) Cl

I-2-52 — CH₂ O H NHOCH₃ (2) Cl (4) Cl

I-2-53 — CH₂ O H NHOCH₃ (2) Cl (4) Cl

I-2-54 — CH₂ O H N(CH₃)O—CH₃ (2) Cl (4) Cl

I-2-55 — CH₂ O H N(CH₃)O—CH₃ (2) Cl (4) Cl

I-2-56 — CH₂ O

(2) Cl (4) Cl

log P = 2.75^(a)) I-2-57 — CH₂ O

(2) Cl (4) Cl

I-2-58 — CH₂ S C₃H₇-i

(2) Cl (4) Cl

log P = 1.91^(a)) I-2-59 — CH₂ O CH₃

(2) Cl (4) Cl

log P = 1.81^(a)) I-2-60 — CH₂ O CH₃

(2) Cl (4) Cl

log P = 1.11^(a)) I-2-61 — CH₂ O CH₃ N(CH₃)₂ (2) Cl (4) Cl

log P = 2.26^(a)) I-2-62 — CH₂ O CH₃ N(CH₃)₂ (2) Cl (4) Cl

log P = 1.48^(a)) I-2-63 — CH₂ S CH₃

(2) Cl (4) SO₂CH₃

log P = 1.81^(a)) I-2-64 — CH₂ S CH₃

(2) Cl (4) SO₂CH₃

log P = 1.00^(a)) I-2-65 — CH₂ O H NH₂ (2) Cl (4) SO₂CH₃

log P = 0.30^(a)) I-2-66 — CH₂ O H

(2) Cl (4) SO₂CH₃

log P = 1.57^(a)) I-2-67 O (CH₂)₂ O H CH₃ (2) Cl (4) Cl

I-2-68 O (CH₂)₂ O H

(2) Cl (4) Cl

log P = 2.28^(a)) I-2-69 O (CH₂)₂ O H OC₃H₇-i (2) Cl (4) Cl

log P = 2.98^(a)) I-2-70 O (CH₂)₂ O H OC₃H₇-i (2) Cl (4) Cl

log P = 2.46^(a)) I-2-71 O (CH₂)₂ O H C₂H₅ (2) Cl (4) Cl

I-2-72 O (CH₂)₂ O H C₂H₅ (2) Cl (4) Cl

log P = 1.64^(a)) I-2-73 O (CH₂)₂ O H

(2) Cl (4) Cl

log P = 1.84^(a)) I-2-74 O (CH₂)₂ O H

(2) Cl (4) Cl

log P = 1.37^(a)) I-2-75 O (CH₂)₂ S H

(2) Cl (4) Cl

log P = 2.23^(a)) I-2-76 O (CH₂)₂ S H

(2) Cl (4) Cl

log P = 1.73^(a)) I-2-77 O (CH₂)₂ O H CF₃ (2) Cl (4) Cl

I-2-78 O (CH₂)₂ O H CF₃ (2) Cl (4) Cl

I-2-79 — CH₂ O H NH₂ (2) Cl (4) SO₂CH₃ log P = 1.23^(a)) I-2-80 — CH₂ OH

(2) Cl (4) SO₂CH₃

log P = 0.74^(a)) I-2-81 — CH₂ O H

(2) Cl (4) SO₂CH₃

log P = 1.58^(a)) I-2-82 — CH₂ O H N(CH₃)₂ (2) Cl (4) SO₂CH₃

log P = 1.58^(a)) I-2-83 — CH₂ O H N(CH₃)₂ (2) Cl (4) SO₂CH₃

log P = 0.77^(a)) I-2-84 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-85 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-86 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-87 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-88 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-89 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-90 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-91 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-92 — CH₂ O H N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-93 — CH₂ O H N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-94 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-95 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-96 — CH₂ O

(2) Cl (4) SO₂CH₃

I-2-97 — CH₂ O

(2) Cl (4) SO₂CH₃

I-2-98 — CH₂ O

NHCH₃ (2) Cl (4) SO₂CH₃

I-2-99 — CH₂ O

NHCH₃ (2) Cl (4) SO₂CH₃

I-2-100 — CH₂ O

NH₂ (2) Cl (4) SO₂CH₃

I-2-101 — CH₂ O

NH₂ (2) Cl (4) SO₂CH₃

I-2-102 — CH₂ O

N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-103 — CH₂ O

N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-104 — CH₂ O CH₃ NHC₂H₅ (2) Cl (4) SO₂CH₃

I-2-105 — CH₂ O CH₃ NHCH₃ (2) Cl (4) SO₂CH₃

I-2-106 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-107 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-108 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-109 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-110 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-111 — CH₂ O H

(2) Cl (4) SO₂CH₃

I-2-112 — CH₂ O

NHCH₃ (2) Cl (4) SO₂CH₃

I-2-113 — CH₂ O

NHCH₃ (2) Cl (4) SO₂CH₃

I-2-114 — CH₂ O

N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-115 — CH₂ O

N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-116 — CH₂ O H NH₂ (2) Cl (4) SO₂CH₃

I-2-117 — CH₂ O H NH₂ (2) Cl (4) SO₂CH₃

I-2-118 O (CH₂)₂ O H NH₂ (2) Cl (4) Cl

log P = 1.66^(a)) I-2-119 O (CH₂)₂ O H NH₂ (2) Cl (4) Cl

log P = 1.22^(a)) I-2-120 — CH₂ O OCH₃ NH₂ (2) Cl (4) Cl

I-2-121 — CH₂ O OCH₃ NH₂ (2) Cl (4) Cl

I-2-122 — CH₂ O OCH₃ NH₂ (2) Cl (4) SO₂CH₃

I-2-123 — CH₂ O OCH₃ NH₂ (2) Cl (4) SO₂CH₃

I-2-124 — CH₂ O OCH₃ NHCH₃ (2) Cl (4) Cl

I-2-125 — CH₂ O OCH₃ NHCH₃ (2) Cl (4) Cl

I-2-126 — CH₂ O OCH₃ NHCH₃ (2) Cl (4) SO₂CH₃

I-2-127 — CH₂ O OCH₃ NHCH₃ (2) Cl (4) SO₂CH₃

I-2-128 — CH₂ O OCH₃ N(CH₃)₂ (2) Cl (4) Cl

I-2-129 — CH₂ O OCH₃ N(CH₃)₂ (2) Cl (4) Cl

I-2-130 — CH₂ O OCH₃ N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-131 — CH₂ O OCH₃ N(CH₃)₂ (2) Cl (4) SO₂CH₃

I-2-132 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-133 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-134 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-135 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-136 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-137 — CH₂ O OCH₃

(2) Cl (4) Cl

I-2-138 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-139 — CH₂ O OCH₃

(2) Cl (4) SO₂CH₃

I-2-140 — CH₂ O H

(2) Cl (4) SO₂CH₃

log P = 2.35^(a)) I-2-141 O (CH₂)₂ O H CH₃ (2) Cl (4) SO₂CH₃

I-2-142 O (CH₂)₂ O H CH₃ (2) Cl (4) SO₂CH₃

I-2-143 O (CH₂)₂ O H C₂H₅ (2) Cl (4) SO₂CH₃

I-2-144 O (CH₂)₂ O H C₂H₅ (2) Cl (4) SO₂CH₃

I-2-145 O

O H CH₃ (2) Cl (4) Cl

I-2-146 O

O H CH₃ (2) Cl (4) Cl

I-2-147 O

O H C₂H₅ (2) Cl (4) Cl

I-2-148 O

O H C₂H₅ (2) Cl (4) Cl

I-2-149 O

O H CH₃ (2) Cl (4) SO₂CH₃

I-2-150 O

O H CH₃ (2) Cl (4) SO₂CH₃

I-2-151 O

O H C₂H₅ (2) Cl (4) SO₂CH₃

I-2-152 O

O H C₂H₅ (2) Cl (4) SO₂CH₃

[0250] TABLE 2 Examples of compounds of the formula (I-3) (I-3)

Ex. (position) (position) No. A¹ A² Q R¹ R² X Y Z Physical data I-3-1 —CH₂ O H NH—NO₂ (2) NO₂ —

m.p.: 191° C. I-3-2 — CH₂ O CH₃ NHCH₃ (2) NO₂ —

I-3-3 — CH₂ O C₂H₅ NHC₂H₅ (2) NO₂ —

I-3-4 — (CH₂)₂ O H CH₃ (2) NO₂ —

I-3-5 — CH₂ O C₃H₇-i

(2) NO₂ —

log P = 2.53^(a)) I-3-6 — CH₂ O C₃H₇-i

(2) NO₂ —

log P = 1.64^(a)) I-3-7 — CH₂ O C₃H₇-i N(CH₃)₂ (2) NO₂ —

log P = 1.63^(a)) I-3-8 — CH₂ O

NHC₂H₅ (2) NO₂ —

log P = 2.60^(a)) I-3-9 — CH₂ O

NHC₂H₅ (2) NO₂ —

log P = 1.75^(a)) I-3-10 — CH₂ O

(2) NO₂ —

log P = 2.94^(a)) I-3-11 — CH₂ O

(2) NO₂ —

log P = 2.05^(a)) I-3-12 — CH₂ O H N(CH₃)₂ (2) NO₂ —

I-3-13 — CH₂ O H N(CH₃)₂ (2) NO₂ —

I-3-14 — CH₂ O H

(2) NO₂ —

I-3-15 — CH₂ O H

(2) NO₂ —

I-3-16 — CH₂ O

(2) NO₂ —

I-3-17 — CH₂ O

(2) NO₂ —

I-3-18 — CH₂ O

NHCH₃ (2) NO₂ —

I-3-19 — CH₂ O

NHCH₃ (2) NO₂ —

I-3-20 — CH₂ O

NH₂ (2) NO₂ —

I-3-21 — CH₂ O

NH₂ (2) NO₂ —

I-3-22 — CH₂ O

N(CH₃)₂ (2) NO₂ —

I-3-23 — CH₂ O

N(CH₃)₂ (2) NO₂ —

I-3-24 — CH₂ O CH₃ NHC₂H₅ (2) NO₂ —

I-3-25 — CH₂ O CH₃ NHCH₃ (2) NO₂ —

log P = 0.68^(a)) I-3-26 — CH₂ O H

(2) NO₂ —

I-3-27 — CH₂ O H

(2) NO₂ —

I-3-28 — CH₂ O H

(2) NO₂ —

I-3-29 — CH₂ O H

(2) NO₂ —

I-3-30 — CH₂ O H

(2) NO₂ —

I-3-31 — CH₂ O H

(2) NO₂ —

I-3-32 — CH₂ O

NHCH₃ (2) NO₂ —

I-3-33 — CH₂ O

NHCH₃ (2) NO₂ —

I-3-34 — CH₂ O

N(CH₃)₂ (2) NO₂ —

I-3-35 — CH₂ O

N(CH₃)₂ (2) NO₂ —

I-3-36 — CH₂ O H NH₂ (2) NO₂ —

I-3-37 — CH₂ O H NH₂ (2) NO₂ —

I-3-38 — CH₂ O CH₃ NHC₂H₅ (2) NO₂ —

I-3-39 — CH₂ O C₃H₇-i

(2) NO₂ —

log P = 3.53^(a)) I-3-40 — CH₂ O C₃H₇-i

(2) NO₂ —

log P = 2.59^(a)) I-3-41 — CH₂ O C₃H₇-i OC₂H₅ (2) NO₂ —

log P = 3.04^(a)) I-3-42 — CH₂ O C₃H₇-i OC₂H₅ (2) NO₂ —

log P = 2.06^(a)) I-3-43 — CH₂ O H OC₂H₅ (2) NO₂ —

I-3-44 — CH₂ O H OC₂H₅ (2) NO₂ —

I-3-45 — CH₂ O H OC₃H₇-i (2) NO₂ —

I-3-46 — CH₂ O H OC₃H₇-i (2) NO₂ —

I-3-47 — CH₂ O CH₃ OC₂H₅ (2) NO₂ —

I-3-48 — CH₂ O CH₃ OC₂H₅ (2) NO₂ —

I-3-49 — CH₂ O H NHOCH₃ (2) NO₂ —

I-3-50 — CH₂ O H NHOCH₃ (2) NO₂ —

I-3-51 — CH₂ O H N(CH₃)OCH₃ (2) NO₂ —

I-3-52 — CH₂ O H N(CH₃)OCH₃ (2) NO₂ —

I-3-53 — CH₂ O C₃H₇-i

(2) CF₃ —

I-3-54 — CH₂ O C₃H₇-i

(2) CF₃ —

I-3-55 — CH₂ O C₃H₇-i

(2) CF₃ —

I-3-56 — CH₂ O C₃H₇-i

(2) CF₃ —

I-3-57 — CH₂ O H N(CH₃)₂ (2) CF₃ —

I-3-58 — CH₂ O H N(CH₃)₂ (2) CF₃ —

I-3-59 — CH₂ O H

(2) CF₃ —

I-3-60 — CH₂ O H

(2) CF₃ —

I-3-61 — CH₂ O H

(2) CF₃ —

I-3-62 — CH₂ O H

(2) CF₃ —

I-3-63 — CH₂ O H

(2) CF₃ —

I-3-64 — CH₂ O H

(2) CF₃ —

I-3-65 — CH₂ O H

(2) CF₃ —

I-3-66 — CH₂ O H

(2) CF₃ —

I-3-67 — CH₂ O H

(2) CF₃ —

I-3-68 — CH₂ O H

(2) CF₃ —

I-3-69 — CH₂ O H

(2) CF₃ —

I-3-70 — CH₂ O H

(2) CF₃ —

I-3-71 — CH₂ O H OC₂H₅ (2) CF₃ —

I-3-72 — CH₂ O H OC₂H₅ (2) CF₃ —

I-3-73 — CH₂ O C₃H₇-i

(2) CF₃ —

I-3-74 — CH₂ O C₃H₇-i

(2) CF₃ —

I-3-75 — CH₂ O C₃H₇-i OC₂H₅ (2) CF₃ —

I-3-76 — CH₂ O C₃H₇-i OC₂H₅ (2) CF₃ —

I-3-77 — CH₂ O H OC₂H₅ (2) CF₃ —

I-3-78 — CH₂ O H OC₂H₅ (2) CF₃ —

I-3-79 — CH₂ O H OC₃H₇-i (2) CF₃ —

I-3-80 — CH₂ O H OC₃H₇-i (2) CF₃ —

I-3-81 — CH₂ O CH₃ OC₂H₅ (2) CF₃ —

I-3-82 — CH₂ O CH₃ OC₂H₅ (2) CF₃ —

I-3-83 — CH₂ O H NHOCH₃ (2) CF₃ —

I-3-84 — CH₂ O H NHOCH₃ (2) CF₃ —

I-3-85 — CH₂ O H N(CH₃)OCH₃ (2) CF₃ —

I-3-86 — CH₂ O H N(CH₃)OCH₃ (2) CF₃ —

I-3-87 — CH₂ O

NHCH₃ (2) CF₃ —

I-3-88 — CH₂ O

NHCH₃ (2) CF₃ —

I-3-89 — CH₂ O

N(CH₃)₂ (2) CF₃ —

I-3-90 — CH₂ O

N(CH₃)₂ (2) CF₃ —

I-3-91 — CH₂ O

OC₂H₅ (2) CF₃ —

I-3-92 — CH₂ O

OC₂H₅ (2) CF₃ —

I-3-93 — CH₂ O CH₃ NHCH₃ (2) CF₃ —

I-3-94 — CH₂ O CH₃ NHCH₃ (2) CF₃ —

I-3-95 — CH₂ O CH₃ N(CH₃)₂ (2) CF₃ —

I-3-96 — CH₂ O CH₃ N(CH₃)₂ (2) CF₃ —

[0251] Log P values given in the tables were determined in accordancewith EEC Directive 79/831 Annex V.A8 by HPLC (High Performance LiquidChromatography) using a reversed-phase column (C 18). Temperature: 43°C.

[0252] (a) Mobile phases for the determination in the acidic range: 0.1%aqueous phosphoric acid, acetonitrile; linear gradient from 10%acetonitrile to 90% acetonitrile—the corresponding measurement resultsin Tables 1 and 2 are labelled a).

[0253] (b) Mobile phases for the determination in the neutral range:0.01 molar aqueous phosphate buffer solution, acetonitrile; lineargradient from 10% acetonitrile to 90% acetonitrile—the correspondingmeasurement results in Tables 1 and 2 are labelled b).

[0254] Calibration was carried out using unbranched alkane-2-ones(having 3 to 16 carbon atoms) with known log P values (determination ofthe log P values by the retention times using linear interpolationbetween two successive alkanones).

[0255] The lambda max values were determined in the maxima of thechromatographic signals using the UV spectra from 200 nm to 400 nm.

[0256] Starting Materials of the Formula (II):

Example (II-1)

[0257]

[0258] Step 1

[0259] 11.7 g (85.1 mmol) of potassium carbonate and, after 15 min, 11.0g (46.9 mmol) of 2-chloro-ethanol tosylate are added to a solution of10.0 g (42.5 mmol) of ethyl 2,4-dichloro-3-hydroxy-benzoate in 100 ml ofacetonitrile. The reaction mixture is stirred at 70° C. for 19 hoursand, after cooling, concentrated under reduced pressure, and 50 ml ofwater and 50 ml of dichloromethane are added to the residue. The organicphase is separated off, washed with water and saturated aqueous sodiumchloride solution, dried over sodium sulphate and filtered. From thefiltrate, the solvent is carefully distilled off under reduced pressure.

[0260] This gives 12.1 g (95% of theory) of ethyl2,4-dichloro-3-(2-chloro-ethoxy)-benzoate as an oil.

[0261] log P=3.76

[0262] Step 2

[0263] A solution of 2.2 g (55.0 mmol) of sodium hydroxide in 40 ml ofwater is added to a solution of 10.0 g (33.6 mmol) of ethyl2,4-dichloro-3-(2-chloro-ethoxy)-benzoate in 70 ml of ethanol. Thereaction mixture is stirred at room temperature (about 20° C.) for 90minutes, and most of the ethanol is removed by evaporation under reducedpressure. The residue is adjusted to pH 1 using conc. hydrochloric acidand extracted with ethyl acetate. The organic phase is separated off,washed with saturated aqueous sodium chloride solution, dried oversodium sulphate and filtered. From the filtrate, the solvent iscarefully distilled off under reduced pressure.

[0264] This gives 9.0 g (99% of theory) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoic acid as a white solid.

[0265] log P=2.31

[0266] Step 3

[0267] A solution of 8.5 g (31.5 mmol) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoic acid in 12 ml of thionylchloride is heated at 60° C. for 1 hour. After the evolution of gas hasceased, the excess thionyl chloride is removed under reduced pressure.

[0268] This gives 9.0 g (99% of theory) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoyl chloride as an oily residue.

[0269] Step 4

[0270] 9.5 g of (94 mmol) of triethylamine, 9 g (31.3 mmol) of2,4-dichloro-3-(2-chloro-ethoxy)-benzoyl chloride and 5 drops ofN,N-dimethylformamide are added successively to a solution of 3.5 g(31.3 mmol) of 1-ethyl-5-hydroxy-1H-pyrazole in 200 ml ofdichloromethane. The reaction mixture is stirred at room temperature(about 20° C.), for 21 hours and then washed with 2N hydrochloric acidand saturated aqueous sodium chloride solution, dried over sodiumsulphate and filtered. From the filtrate, the solvent is removed underreduced pressure.

[0271] The oily residue is dissolved in 200 ml of acetonitrile, 17 g(168 mmol) of triethylamine and 3.26 g (38 mmol) of2-hydroxy-2-methyl-propionitrile are added and the mixture is stirred atroom temperature for another 20 hours. Most of the solvent is thenremoved under reduced pressure and the oily residue is taken up in 100ml of dichloromethane. The organic phase is washed with 2N hydrochloricacid and with saturated aqueous sodium chloride solution, dried oversodium sulphate and filtered. The filtrate is freed from the solventunder reduced pressure.

[0272] This gives 11.1 g (98% of theory) of[2,4-dichloro-3-(2-chloro-ethoxy)-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanoneas an orange-yellow crystalline solid.

[0273] log P=2.73.

[0274] Step 5

[0275] A solution of 8.0 g (22 mmol) of[2,4-dichloro-3-(2-chloro-ethoxy)-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanonein 150 ml of tetrahydrofuran and 200 ml of ammonia is heated in anautoclave at 90° C. for 6.5 hours. Most of the excess ammonia isevaporated off and the product that settles out is removed by filtrationand dried under reduced pressure.

[0276] This gives 4.3 g (57% of theory) of[3-(2-amino-ethoxy)-2,4-dichloro-phenyl]-(1-ethyl-5-hydroxy-1H-pyrazol-4-yl)-methanoneas a light-yellow crystalline solid.

[0277] log P=0.72.

[0278] Analogously to Example (II-1), it was also possible to prepare,for example, the compounds of the general formula (II) listed in Table 3below.

TABLE 3 Examples of compounds of the formula (II) Ex. (position)(position) (position) No. —A¹—A²—NHR¹ X Y Z 11-2

(2) Cl (4) Cl

11-3

(2) Cl (4) SO₂CH₃

11-4

(2) Cl (4) Cl

11-5

(2) Cl (4) SO₂CH₃

11-6

(2) Cl (4) Cl

11-7

(2) Cl (4) SO₂CH₃

11-8

(2) Cl (4) Cl

[0279] Starting Materials of the Formula (IV):

Example (IV-1)

[0280]

[0281] Step 1

[0282] At room temperature (about 20° C.) 15 g (59 mmol) of methyl2,4-dichloro-3-bromomethyl-benzoate and then 7.5 g (77 mmol) ofpotassium thiocyanate are introduced into 60 ml of acetonitrile. Thereaction mixture is slowly heated to reflux and then stirred at thistemperature under reflux for 20 hours. After cooling to roomtemperature, the solvent is stripped off under reduced pressure and theresidue is stirred with 70 ml of diethyl ether. Undissolved componentsare filtered off with suction, the solvent is removed under reducedpressure and the residue is distilled under reduced pressure.

[0283] This gives 2.7 g (17% of theory) of methyl2,4-dichloro-3-isocyanatomethyl-benzoate as an oil which is reactedfurther without further purification.

[0284] Step 2

[0285] 5.6 g of crude methyl 2,4-dichloro-3-isocyanatomethyl-benzoateare dissolved in 20 ml of ethanol, and 1.2 g (20 mmol) of 2-propanamineare added. The mixture is heated at the boil for 1 hour, the amount ofsolvent is reduced to one third of the original volume and the productis filtered off with suction.

[0286] This gives 1.7 g (9%, based on methyl2,4-dichloro-3-methyl-benzoate) of methyl2,4-dichloro-3-[[[(isopropylamino)-thioxomethyl]-amino]-methyl]-benzoateas a solid (MS: M⁺=355, 2 Cl according to the isotope pattern).

[0287] Step 3

[0288] 5 g (15 mmol) ofN-(3-methoxycarbonyl-2,6-dichloro-benzyl)-N′-isopropyl-thiourea aredissolved in 30 ml of methanol, and 10 ml (50 mmol) of a 30% strengthsolution of sodium methoxide in methanol are added. Over a period of 30minutes, 50 ml of water are added dropwise, and the mixture is then keptat 60° C. for 2 hours. Following neutralization with 2N hydrochloricacid, the product is filtered off with suction and dried.

[0289] This gives 4.4 g (91% of theory) of2,4-dichloro-3-[[[(isopropylamino)-thioxomethyl]-amino]-methyl]-benzoicacid as a solid of melting point>220° C.

[0290] Analogously to Example (IV-1), it is also possible to prepare,for example, the compounds of the general formula (IVa) listed in Table4 below.

TABLE 4 Examples of compounds of the formula (IVa) Ex. No.

(position) X (position) Y R Physical Data IV-2

(2) Cl (4) Cl CH₃ log P = 0.89^(a)) IV-3

(2) Cl (4) Cl CH₃ m.p.: 195° C. IV-4

(2) Cl (4) Cl CH₃ m.p.: 140° C. IV-5

(2) Cl (4) Cl H m.p.: 175° C. IV-6

(2) Cl (4) Cl CH₃ m.p.: 81° C. IV-7

(2) NO₂ — CH₃ n_(D) ²⁰ = 1.5361 IV-8

(2) Cl (4) Cl H m.p. >260° C. IV-9

(2) Cl (4) Cl CH₃ m.p.: 76° C.  IV-10

(2) NO₂ — H m.p.: >220° C.  IV-11

(2) NO₂ — H m.p.: 210° C.  IV-12

(2) Cl (4) Cl CH₃ m.p.: 147° C.  IV-13

(2) Cl (4) Cl H m.p.: 173° C.

USE EXAMPLES Example A

[0291] Pre-Emergence Test

[0292] Solvent: 5 parts by weight of acetone

[0293] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0294] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0295] Seeds of the test plants are sown in normal soil. After 24 hours,the soil is sprayed with the preparation of active compound such thatthe particular amount of active compound desired is applied per unitarea. The concentration of active compound in the spray liquor is chosensuch that the particular amount of active compound desired is applied in1000 litres of water per hectare.

[0296] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control. Thefigures denote:

[0297] 0%=no effect (like untreated control)

[0298] 100%=total destruction

[0299] In this test, for example, the compounds of Preparation Examples(I-2-1), (I-2-3), (I-2-5) and (I-2-6) exhibit strong activity againstweeds, and some are tolerated well by crop plants, such as, for example,maize, soya beans and wheat.

Example B

[0300] Post-emergence Test

[0301] Solvent: 5 part by weight of acetone

[0302] Emulsifier: 1 part by weight of alkylaryl polyglycol ether

[0303] To produce a suitable preparation of active compound, 1 part byweight of active compound is mixed with the stated amount of solvent,the stated amount of emulsifier is added and the concentrate is dilutedwith water to the desired concentration.

[0304] Test plants of a height of 5-15 cm are sprayed with thepreparation of active compound such that the particular amounts ofactive compound desired are applied per unit area. The concentration ofthe spray liquor is chosen such that the particular amounts of activecompound desired are applied in 1000 l of water/ha.

[0305] After three weeks, the degree of damage to the plants is rated in% damage in comparison to the development of the untreated control. Thefigures denote:

[0306] 0%=no effect (like untreated control)

[0307] 100%=total destruction

[0308] In this test, for example, the compounds of Preparation Examples(I-2-1), (I-2-3), (I-2-4), (I-2-5), (I-2-6), (I-2-7) and (I-2-8) exhibitstrong some are tolerated well by crop plants, such as, for example,maize, oilseed rape and wheat.

1. Compounds of the formula (I)

in which A¹ represents a single bond or represents O, S, SO, SO₂, A²represents alkanediyl (alkylene), alkenediyl or alkinediyl, Q representsO (oxygen) or S (sulphur), R¹ represents hydrogen or represents in eachcase optionally substituted alkyl, alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylamino, dialkylamino, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aryl or arylalkyl, or represents the grouping —C(Q)-R²,R² represents hydrogen, amino, cyanoamino, nitroamino, hydroxyamino,hydrazino, or represents in each case optionally substituted alkyl,alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylamino,dialkylamino, alkoxyamino, N-alkyl-alkoxyamino, alkylhydrazino,dialkylhydrazino, alkenyl, alkenyloxy, alkenylamino, alkenyloxyamino,alkinyl, alkinyloxy, alkinylamino, cycloalkyl, cycloalkyloxy,cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy,cycloalkylalkylamino, aryl, arylcarbonyl, aryloxy, aryloxycarbonyl,arylthio, arylamino, arylhydrazino, arylalkyl, arylalkoxy,arylalkylthio, arylalkylamino, heterocyclyl, heterocyclyloxy,heterocyclylthio, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino, Xrepresents hydrogen, nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl,halogen, or represents in each case optionally substituted alkyl,alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino,dialkylamino or dialkylaminosulphonyl, Y represents hydrogen, nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, halogen, or represents ineach case optionally substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl, and Z represents one of the groupings below

where m represents the numbers 0 to 6, R³ represents hydrogen, halogenor represents in each case optionally substituted alkyl, alkylthio oraryl, or—if m represents 2—optionally also together with a secondradical R³ represents oxygen or alkanediyl (alkylene), R⁴ representshydroxyl, formyloxy, halogen, or represents in each case optionallysubstituted alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy,alkylsulphonyloxy, alkenyloxy, alkinyloxy, aryloxy, arylthio,arylsulphinyl, arylsulphonyl, arylcarbonyloxy, arylcarbonylalkoxy,arylsulphonyloxy, arylalkoxy, arylalkylthio, arylalkylsulphinyl orarylalkylsulphonyl, R⁵ represents hydrogen, cyano, carbamoyl,thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkoxy, alkylthio, alkylsulphinyl, alkylsulphonyl,alkoxycarbonyl or cycloalkyl, R⁶ represents hydrogen or represents ineach case optionally substituted alkyl, alkenyl, alkinyl, cycloalkyl,cycloalkylalkyl, aryl or arylalkyl, R⁷ represents hydroxyl, formyloxy,or represents in each case optionally substituted alkoxy,alkylcarbonyloxy, alkoxycarbonyloxy, alkylaminocarbonyloxy,alkylsulphonyloxy, alkenyloxy, alkinyloxy, arylalkoxy, arylcarbonyloxy,arylcarbonylalkoxy or arylsulphonyloxy, R⁸ represents hydrogen, cyano,carbamoyl, thiocarbamoyl, halogen, or represents in each case optionallysubstituted alkyl, alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl, R⁹ represents hydrogen or representsin each case optionally substituted alkyl or cycloalkyl, R¹⁰ representshydrogen or represents in each case optionally substituted alkyl orcycloalkyl, and R¹¹ represents hydrogen, cyano, carbamoyl, halogen, orrepresents in each case optionally substituted alkyl, alkoxy,alkoxycarbonyl, alkylthio, alkylsulphinyl or alkylsulphonyl. 2.Compounds of the formula (I) according to claim 1, characterized in thatA¹ represents O or represents a single bond, A² represents alkanediyl(alkylene), alkenediyl or alkinediyl having in each case up to 6 carbonatoms, Q represents O (oxygen), R¹ represents hydrogen, represents ineach case optionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl or alkylamino having in eachcase 1 to 6 carbon atoms in the alkyl groups, represents dialkylaminohaving in each case 1 to 4 carbon atoms in the alkyl groups, representsin each case optionally cyano- or halogen-substituted alkenyl or alkinylhaving in each case 2 to 6 carbon atoms, represents in each caseoptionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl orcycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy- orC₁-C₄-halogenoalkoxy-substituted aryl or arylalkyl having in each case 6or 10 carbon atoms in the aryl group and optionally 1 to 4 carbon atomsin the alkyl moiety, or represents the grouping —C(Q)-R², R² representshydrogen, amino, cyanoamino, nitroamino, hydroxyamino, hydrazino,represents C₁-C₄-alkyl-carbonyl, represents C₁-C₄-alkoxycarbonyl,represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio, alkylamino,alkoxyamino or alkylhydrazino having in each case 1 to 6 carbon atoms inthe alkyl groups, represents dialkylamino, N-alkyl-alkoxyamino ordialkylhydrazino having in each case 1 to 4 carbon atoms in the alkylgroups, represents in each case optionally halogen-substituted alkenyl,alkenyloxy, alkenylamino, alkenyloxyamino, alkinyl, alkinyloxy oralkinylamino having in each case 2 to 6 carbon atoms, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkyl,cycloalkyloxy, cycloalkylamino, cycloalkylalkyl, cycloalkylalkoxy orcycloalkylalkylamino having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-, C₁-C₄-halogenoalkoxy-or C₁-C₄-alkoxy-carbonyl-substituted aryl, aryl-carbonyl, aryloxy,aryloxycarbonyl, arylthio, arylamino, arylhydrazino, arylalkyl,arylalkoxy, arylalkylthio or arylalkylamino having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety, or represents in each case optionally nitro-, cyano-,halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio- orC₁-C₄-alkoxy-carbonyl-substituted monocyclic or bicyclic heterocyclyl,heterocyclyloxy, heterocyclylthio, heterocyclylamino, heterocyclylalkyl,heterocyclylalkoxy, heterocyclylalkylthio or heterocyclylalkylamino,where in each case the heterocyclyl grouping contains up to 10 carbonatoms and additionally at least one heteroatom selected from the groupconsisting of nitrogen (N) (but at most 5 N atoms), oxygen (O) (but atmost 2 O atoms), sulphur (S) (but at most 2 S atoms), SO and SO₂ andalso optionally additionally one group selected from the groupconsisting of oxo (C═O), thioxo (C═S), imino (C═NH), cyanoimino (C═N—CN)and nitroimino (C═N—NO₂), X represents hydrogen, nitro, cyano, carboxyl,carbamoyl, thio-carbamoyl, halogen, or represents in each caseoptionally cyano-, halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-,C₁-C₄-alkylsulphinyl- or C₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy,alkylthio, alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylamino-sulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups, Y represents hydrogen, nitro, cyano, carboxyl, carbamoyl,thio-carbamoyl, halogen, or represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl, alkylamino, dialkylamino ordialkylaminosulphonyl having in each case 1 to 6 carbon atoms in thealkyl groups, Z represents one of the groupings below,

m represents the numbers 0 to 3, R³ represents hydrogen, halogen,represents in each case optionally cyano-, halogen-, C₁-C₄-alkoxy-,C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl or alkylthio having in each case1 to 6 carbon atoms, or represents phenyl, or if m represents2—optionally also together with a second radical R³ represents oxygen oralkanediyl (alkylene) having 3 to 5 carbon atoms, R⁴ representshydroxyl, formyloxy, halogen, represents in each case optionally cyano-,halogen-, C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkoxy, alkylthio, alkylsulphinyl,alkylsulphonyl, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy or alkylsulphonyloxy having in each case 1 to 6carbon atoms, represents in each case optionally halogen-substitutedalkenyloxy or alkinyloxy having in each case 3 to 6 carbon atoms,represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-halogenoalkylsulphinyl-,C₁-C₄-alkylsulphonyl- or C₁-C₄-halogeno-alkylsulphonyl-substitutedaryloxy, arylthio, arylsulphinyl, arylsulphonyl, arylcarbonyloxy,arylcarbonylalkoxy, arylsulphonyloxy, arylalkoxy, arylalkylthio,arylalkylsulphinyl or arylalkylsulphonyl having in each case 6 or 10carbon atoms in the aryl group and optionally 1 to 4 carbon atoms in thealkyl moiety, R⁵ represents hydrogen, cyano, carbamoyl, thiocarbamoyl,halogen, represents in each case optionally cyano-, halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl, alkoxy, alkylthio,alkylsulphinyl, alkylsulphonyl or alkoxycarbonyl having in each case 1to 6 carbon atoms in the alkyl groups or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms. R⁶ represents hydrogen, represents optionally cyano-, halogen-,C₁-C₄-alkoxy-, C₁-C₄-alkylthio-, C₁-C₄-alkylsulphinyl- orC₁-C₄-alkylsulphonyl-substituted alkyl having 1 to 6 carbon atoms,represents in each case optionally cyano- or halogen-substituted alkenylor alkinyl having in each case 3 to 6 carbon atoms, represents in eachcase optionally cyano-, halogen- or C₁-C₄-alkyl-substituted cycloalkylor cycloalkylalkyl having in each case 3 to 6 carbon atoms in thecycloalkyl group and optionally 1 to 4 carbon atoms in the alkyl moiety,or represents in each case optionally nitro-, cyano-, halogen-,C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-halogenoalkylsulphinyl-,C₁-C₄-alkylsulphonyl- or C₁-C₄-halogeno-alkylsulphonyl-substituted arylor arylalkyl having in each case 6 or 10 carbon atoms in the aryl groupand optionally 1 to 4 carbon atoms in the alkyl moiety, R⁷ representshydroxyl, formyloxy, represents in each case optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkoxy, alkylcarbonyloxy, alkoxycarbonyloxy,alkylaminocarbonyloxy or alkylsulphonyloxy having in each case 1 to 6carbon atoms in the alkyl groups, represents in each case optionallycyano-, or halogen-substituted alkenyloxy or alkinyloxy having in eachcase 3 to 6 carbon atoms, or represents in each case optionally nitro-,cyano-, halogen-, C₁-C₄-alkyl-, C₁-C₄-halogenoalkyl-, C₁-C₄-alkoxy-,C₁-C₄-halogenoalkoxy-, C₁-C₄-alkylthio-, C₁-C₄-halogenoalkylthio-,C₁-C₄-alkylsulphinyl-, C₁-C₄-halogenoalkylsulphinyl-,C₁-C₄-alkylsulphonyl- or C₁-C₄-halogenoalkylsulphonyl-substitutedarylalkoxy, arylcarbonyloxy, arylcarbonyl-alkoxy or arylsulphonyloxyhaving in each case 6 or 10 carbon atoms in the aryl group andoptionally 1 to 4 carbon atoms in the alkyl moiety, R⁸ representshydrogen, cyano, carbamoyl, thiocarbamoyl, halogen, or represents ineach case optionally cyano-, halogen- or C₁-C₄-alkoxy-substituted alkyl,alkylcarbonyl, alkoxy, alkoxycarbonyl, alkylthio, alkylsulphinyl oralkylsulphonyl having in each case 1 to 6 carbon atoms in the alkylgroups, R⁹ represents hydrogen, represents optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkyl, or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms, R¹⁰ represents hydrogen, represents optionally cyano-, halogen-or C₁-C₄-alkoxy-substituted alkyl, or represents optionally cyano-,halogen- or C₁-C₄-alkyl-substituted cycloalkyl having 3 to 6 carbonatoms, and R¹¹ represents hydrogen, cyano, carbamoyl, halogen, orrepresents in each case optionally cyano-, halogen- orC₁-C₄-alkoxy-substituted alkyl, alkoxy, alkoxycarbonyl, alkylthio,alkylsulphinyl or alkylsulphonyl having in each case 1 to 6 carbon atomsin the alkyl groups.
 3. Compounds of the formula (I) according to claim1, characterized in that A² represents methylene (—CH₂—),ethane-1,1-diyl (—CH(CH₃)—), ethane-1,2-diyl (dimethylene, —CH₂CH₂—),propane-1,1-diyl (—CH(C₂H₅)—), propane-1,2-diyl (—CH(CH₃)CH₂—),propane-1,3-diyl (—CH₂CH₂CH₂—), butane-1,3-diyl (—CH(CH₃)CH₂CH₂—),butane-1,4-diyl (—CH₂CH₂CH₂CH₂—), ethenediyl, propenediyl, butenediyl,ethinediyl, propinediyl or butinediyl, R¹ represents hydrogen,represents in each case optionally cyano-, fluorine-, chlorine-,bromine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, n- ori-propylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, n-, i-, s- ort-pentyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, methylamino, ethylamino, n- ori-propyl-amino, n-, i-, s- or t-butylamino, represents dimethylamino ordiethylamino, represents in each case optionally fluorine-, chlorine-and/or bromine-substituted ethenyl, propenyl, butenyl, pentenyl,ethinyl, propinyl, butinyl or pentinyl, represents in each caseoptionally cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl- orpropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,naphthyl, phenylmethyl, phenylethyl, naphthylmethyl or naphthylethyl orrepresents the grouping —C(Q)-R², R² represents hydrogen, amino,cyanoamino, nitroamino, hydroxyamino, hydrazino, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, n- or i-propylsulphinyl-,methylsulphonyl- or ethylsulphonyl-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, n-, i-, s- or t-pentyl, methoxy,ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio,n- or i-propylthio, n-, i-, s- or t-butylthio, methylamino, ethylamino,n- or i-propylamino, n-, i-, s- or t-butylamino, methoxyamino,ethoxyamino, n- or i-propoxyamino, n-, i-, s- or t-butoxyamino,methyl-hydrazino, ethylhydrazino, n- or i-propylhydrazino, n-, i-, s- ort-butylhydrazino, represents dimethylamino, diethylamino,N-methyl-methoxyamino, dimethylhydrazino or diethylhydrazino, representsin each case optionally fluorine-, chlorine- and/or bromine-substitutedethenyl, propenyl, butenyl, pentenyl, ethinyl, propinyl, butinyl,pentinyl, propenyloxy, butenyloxy, pentenyloxy, propenylthio,butenylthio, pentenylthio, propenylamino, butenylamino, pentenylamino,propenyloxyamino, butenyloxyamino, pentenyloxyamino, ethinyl, propinyl,butinyl, pentinyl, propinyloxy, butinyloxy, pentinyloxy, propinylamino,butinylamino or pentinylamino, represents in each case optionallycyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl- orpropyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropyloxy, cyclobutyloxy, cyclopentyloxy, cyclohexyloxy,cyclopropylamino, cyclobutylamino, cyclopentylamino, cyclohexylamino,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl,cyclohexylmethyl, cyclopropylmethoxy, cyclobutylmethoxy,cyclopentylmethoxy, cyclohexylmethoxy, cyclopropylmethylamino,cyclobutylmethylamino, cyclopentylmethylamino or cyclohexylmethylamino,represents in each case optionally nitro-, cyano-, fluorine-, chlorine-,bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,di-fluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-,ethoxy-carbonyl-, n- or i-propoxycarbonyl-substituted phenyl,phenylcarbonyl, phenoxy, phenoxycarbonyl, phenylthio, phenylamino,phenylhydrazino, naphthyl, naphthyloxy, naphtylthio, naphthylamino,phenylmethyl, phenylethyl, phenylmethoxy, phenylethoxy,phenylmethylthio, phenylethylthio, phenylmethylamino, phenylethylamino,naphthylmethyl, naphthylethyl, naphthylmethoxy, naphthylethoxy,naphthylmethylamino or naphthylethylamino, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, difluoromethyl-,trifluoro-methyl-, dichloromethyl-, trichloromethyl-,chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, n-, i-, s- or t-butoxy-, difluoromethoxy-,trifluoromethoxy-, methylthio-, ethylthio-, n- or i-propylthio-, n-, i-,s- or t-butylthio-, difluoromethylthio-, trifluoromethylthio-,methoxycarbonyl-, ethoxycarbonyl-, n- or i-propoxycarbonyl-substitutedmonocyclic or bicyclic heterocyclyl, heterocyclyloxy, heterocyclylamino,heterocyclylalkyl, heterocyclylalkoxy or heterocyclylalkylamino from thegroup consisting of furyl, furyloxy, furylamino, furylmethyl,furylmethoxy, furylmethylamino, thienyl, thienylmethyl, pyrrolidinyl,pyrrolidinylamino, oxopyrrolidinyl, pyrrolyl, indolyl, pyrrolylmethyl,pyrazolyl, pyrazolyloxy, pyrazolylamino, pyrazolylmethyl, imidazolyl,imidazolylmethyl, 2-oxo-1,3-diaza-cyclopentyl, oxazolyl, dihydrooxazolyl(oxazolinyl), isoxazolyl, dihydroisoxazolyl (isoxazolinyl),tetrahydroisoxazolyl (isoxazolidinyl), oxazolylmethyl, thiazolyl,dihydrothiazolyl (thiazolinyl), tetrahydrothiazolyl (thiazolidinyl),thiazolylmethyl, thiazolidinyl, oxothiazolidinyl,cyanoiminothiazolidinyl, oxotriazolinyl, oxotetrazolinyl, piperidinyl,piperidinylamino, oxopiperidinyl, 2-oxo-1,3-diaza-cyclohexyl, 2-oxo- 1-aza-cycloheptyl, 2-oxo-1,3-diazacycloheptyl, morpholinyl,morpholinylamino, piperazinyl, pyridinyl, pyridinyloxy, pyridinylamino,pyridinylmethyl, pyridinylmethoxy, pyrimidinyl, pyrimidinyloxy,pyrimidinylmethyl, pyrimidinylmethoxy, X represents hydrogen, nitro,cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine, bromine,iodine, or represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonyl-substituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- ori-propoxy, n-, i-, s- or t-butoxy, methylthio, ethylthio, n- ori-propylthio, n-, i-, s- or t-butylthio, methylsulphinyl,ethylsulphinyl, n- or i-propylsulphinyl, methylsulphonyl,ethylsulphonyl, n- or i-propylsulphonyl, methylamino, ethylamino, n- ori-propylamino, n-, i-, s- or t-butylamino, dimethylamino, diethylamino,dimethylaminosulphonyl or diethylaminosulphonyl, Y represents hydrogen,nitro, cyano, carboxyl, carbamoyl, thiocarbamoyl, fluorine, chlorine,bromine, iodine, or represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-, ethylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, n-, i-, s- or t-butoxy,methylthio, ethylthio, n- or i-propylthio, n-, i-, s- or t-butylthio,methylsulphinyl, ethylsulphinyl, n- or i-propylsulphinyl,methylsulphonyl, ethylsulphonyl, n- or i-propylsulphonyl, methylamino,ethylamino, n- or i-propylamino, n-, i-, s- or t-butylamino,dimethylamino, diethylamino, dimethylaminosulphonyl ordiethylaminosulphonyl m represents the number 0, 1 or 2, R³ representsfluorine, chlorine or bromine, represents in each case optionallycyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-,methylthio-, ethylthio-, n- or i-propylthio-, methylsulphinyl-,ethylsulphinyl-, methylsulphonyl- or ethylsulphonylsubstituted methyl,ethyl, n- or i-propyl, n-, i-, s- or t-butyl, methylthio, ethylthio, n-or i-propylthio, n-, i-, s- or t-butylthio, or represents phenyl, or—ifm represents 2,—optionally also together with a second radical R³represents oxygen, propane-1,3-diyl or butane-1,4-diyl, R⁴ representshydroxyl, formyloxy, fluorine or chlorine, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl, ethylsulphonyl, acetyloxy, propionyloxy, n- ori-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n-or i-propylsulphonyloxy, represents in each case optionally fluorine-,chlorine- and/or bromine-substituted propenyloxy, butenyloxy,propinyloxy or butinyloxy, represents in each case optionally nitro-,cyano-, fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, n-, i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, difluoromethylthio-,trifluoromethylthio-, methylsulphinyl-, ethylsulphinyl-,trifluoromethylsulphinyl-, methylsulphonyl-, ethylsulphonyl- ortrifluoromethylsulphonyl-substituted phenyloxy, phenylthio,phenylsulphinyl, phenylsulphonyl, phenylcarbonyloxy,phenylcarbonylalkoxy, phenylsulphonyloxy, phenylmethoxy,phenylmethylthio, phenylmethylsulphinyl or phenylmethylsulphonyl, R⁵represents hydrogen, cyano, carbamoyl, thiocarbamoyl, fluorine, chlorineor bromine, represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-,n- or i-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl-or ethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s-or t-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylsulphinyl, ethylsulphinyl, methylsulphonyl,ethylsulphonyl, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, or represents in each case optionally cyano-,fluorine-, chlorine-, methyl- or ethyl-substituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, R⁶ represents hydrogen,represents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-, methylthio-, ethylthio-, n- ori-propylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, represents in each case optionally cyano-, fluorine-, chlorine-or bromine-substituted propenyl, butenyl, propinyl or butinyl,represents in each case optionally cyano-, fluorine-, chlorine-, methyl-or ethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, n-, i-, s- or t-butylthio-,difluoromethylthio-, trifluoromethylthio-, methylsulphinyl-,ethylsulphinyl-, trifluoromethylsulphinyl-, methylsulphonyl,ethylsulphonyl- or trifluoromethylsulphonyl-substituted phenyl orphenylmethyl, R⁷ represents hydroxyl, formyloxy, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy, orrepresents in each case optionally cyano-, fluorine-, chlorine- orbromine-substituted propenyloxy, butenyloxy, propinyloxy or butinyloxy,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-, i-, s- ort-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy-, trifluoromethoxy-, methylthio-, ethylthio-, n- ori-propylthio-, difluoromethyl-thio-, trifluoromethylthio-,methylsulphinyl-, ethylsulphinyl-, trifluoromethylsulphinyl-,methylsulphonyl-, ethylsulphonyl- ortrifluoromethylsulphonyl-substituted phenylmethoxy, phenylcarbonyloxy,phenylcarbonylmethoxy or phenylsulphonyloxy, R⁸ represents hydrogen,cyano, carbamoyl, thiocarbamoyl, fluorine, chlorine or bromine, orrepresents in each case optionally cyano-, fluorine-, chlorine-,methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl, n- ori-propyl, n-, i-, s- or t-butyl, acetyl, propionyl, n- or i-butyroyl,methoxy, ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl, R⁹represents hydrogen, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents ineach case optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,R¹⁰ represents hydrogen, represents in each case optionally cyano-,fluorine-, chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substitutedmethyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl, or represents ineach case optionally cyano-, fluorine-, chlorine-, methyl- orethyl-substituted cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl,and R¹¹ represents hydrogen, cyano, carbamoyl, fluorine, chlorine orbromine or represents in each case optionally cyano-, fluorine-,chlorine-, methoxy-, ethoxy-, n- or i-propoxy-substituted methyl, ethyl,n- or i-propyl, n-, i-, s- or t-butyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl.
 4. Compounds of the formula (I)according to claim 1, characterized in that A² represents methylene(—CH₂—), ethane-1,2-diyl (dimethylene, —CH₂CH₂—) or propane-1,3-diyl(—CH₂CH₂CH₂—), R¹ represents hydrogen, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, methylthio-,ethylthio-, methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n- or i-butyl,represents methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n-or i-propylthio, methylamino, ethylamino, n- or i-propylamino,represents dimethylamino, represents in each case optionally fluorine-and/or chlorine-substituted propenyl, butenyl, ethinyl, propinyl orbutinyl, represents in each case optionally cyano-, fluorine-, chlorine-or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl,cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, or represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy- or trifluoromethoxy-substituted phenyl,phenylmethyl or phenylethyl, or represents the grouping —C(Q)-R², R²represents hydrogen, amino, hydroxyamino, hydrazino, represents in eachcase optionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-, methylthio-, ethylthio-, n- or i-propylthio-,methylsulphinyl-, ethylsulphinyl-, methylsulphonyl- orethylsulphonyl-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- ort-butyl, methoxy, ethoxy, n- or i-propoxy, methylthio, ethylthio, n- ori-propylthio, methylamino, ethylamino, n- or i-propylamino,methoxyamino, ethoxyamino, n- or i-propoxyamino, representsdimethylamino, represents N-methyl-methoxyamino, representsdimethylhydrazino, represents in each case optionally fluorine- and/orchlorine-substituted ethenyl, propenyl, butenyl, propenyloxy,butenyloxy, propenylthio, butenylthio, propenylamino, butenylamino,ethinyl, propinyl, butinyl, propinyloxy, butinyloxy, propinylamino orbutinylamino, represents in each case optionally cyano-, fluorine-,chlorine- or methyl-substituted cyclopropyl, cyclobutyl, cyclopentyl,cyclohexyl, cyclopropylmethyl, cyclobutylmethyl, cyclopentylmethyl orcyclohexylmethyl, represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- or i-propyl-, n-,i-, s- or t-butyl-, trifluoromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methoxycarbonyl-,ethoxycarbonyl-, n- or i-propoxycarbonyl-substituted phenyl,phenylamino, phenylmethyl or phenylethyl, or represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-, methyl-,ethyl-, n- or i-propyl-, n-, i-, s- or t-butyl-, difluoromethyl-,trifluoromethyl-, dichloromethyl-, trichloromethyl-,chlorodifluoromethyl-, fluorodichloromethyl-, methoxy-, ethoxy-, n- ori-propoxy-, difluoromethoxy-, trifluoromethoxy-, methylthio-,ethylthio-, n- or i-propylthio-, difluoromethylthio-,trifluoromethylthio-, methoxycarbonyl-, ethoxycarbonyl-, n- ori-propoxycarbonyl-substituted monocyclic or bicyclic heterocyclyl orheterocyclylalkyl from the group consisting of furyl, furylmethyl,thienyl, thienylmethyl, pyrrolidinyl, oxopyrrolidinyl, pyrrolyl,pyrrolylmethyl, pyrazolyl, pyrazolylmethyl, imidazolyl,imidazolylmethyl, 2-oxo- 1,3-diazacyclopentyl, oxazolyl, isoxazolyl,oxazolylmethyl, isoxazolidinyl, thiazolyl, thiazolylmethyl, piperidinyl,oxo-piperidinyl, 2-oxo-1,3-diazacyclohexyl, morpholinyl, piperazinyl,pyridinyl, pyridinylmethyl, pyrimidinyl, pyrimidinylmethyl, X representshydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl,ethyl, n- or i-propyl, difluoromethyl, trifluoromethyl, dichloromethyl,trichloromethyl, methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methyl-sulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, Y represents hydrogen, nitro, cyano, fluorine,chlorine, bromine, iodine, methyl, ethyl, difluoromethyl,trifluoromethyl, dichloromethyl, trichloromethyl, methoxymethyl,methylthiomethyl, methylsulphinylmethyl, methylsulphonylmethyl, methoxy,ethoxy, difluoromethoxy, trifluoromethoxy, methylthio, ethylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylamino-sulphonyl, m represents the number 0 or 1, R³ representshydrogen, represents in each case optionally fluorine- and/orchlorine-substituted methyl, ethyl, n- or i-propyl, methylthio,ethylthio, n- or i-propylthio, or represents phenyl, or—if m represents2—optionally also together with a second radical R³ represents oxygen,propane-1,3-diyl or butane-1,4-diyl, R⁴ represents hydroxyl, representsformnyloxy, represents in each case optionally fluorine- and/orchlorine-substituted methoxy, ethoxy, n- or i-propoxy, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl, ethylsulphonyl, acetyloxy, propionyloxy, n- ori-butyroyloxy, methoxycarbonyloxy, ethoxycarbonyloxy, n- ori-propoxycarbonyloxy, methylaminocarbonyloxy, ethylaminocarbonyloxy, n-or i-propylaminocarbonyloxy, methylsulphonyloxy, ethylsulphonyloxy, n-or i-propylsulphonyloxy, represents in each case optionally fluorine-and/or chlorine-substituted propenyloxy, butenyloxy, propinyloxy orbutinyloxy, represents in each case optionally nitro-, cyano-,fluorine-, chlorine-, brominemethyl-, ethyl-, n- or i-propyl-,trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-, difluoromethoxy-or trifluoromethoxy-substituted phenyloxy, phenylthio, phenylsulphinyl,phenylsulphonyl, phenylcarbonyloxy, phenylcarbonylmethoxy,phenylsulphonyloxy, phenylmethoxy, phenylmethylthio,phenylmethylsulphinyl or phenylmethylsulphonyl, R⁵ represents hydrogen,cyano, fluorine, chlorine, represents in each case optionally fluorine-and/or chlorine-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl, ethylsulphonyl,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, or representsin each case optionally cyano-, fluorine-, chlorine- ormethyl-substituted cyclopropyl, R⁶ represents hydrogen, represents ineach case optionally cyano-, fluorine-, chlorine-, methoxy orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,represents in each case optionally fluorine- or chlorine-substitutedpropenyl, butenyl, propinyl or butinyl, represents in each caseoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, or represents in each caseoptionally fluorine-, chlorine-, bromine-, methyl-, ethyl-, n- ori-propyl-, trifluoromethyl-, methoxy-, ethoxy-, n- or i-propoxy-,difluoromethoxy- or trifluoromethoxy-substituted phenyl or phenylmethyl,R⁷ represents hydroxyl, represents formyloxy, represents in each caseoptionally cyano-, fluorine-, chlorine-, methoxy-, ethoxy-, n- ori-propoxy-substituted methoxy, ethoxy, n- or i-propoxy, acetyloxy,propionyloxy, n- or i-butyroyloxy, methoxycarbonyloxy,ethoxycarbonyloxy, n- or i-propoxycarbonyloxy, methylaminocarbonyloxy,ethylaminocarbonyloxy, n- or i-propylaminocarbonyloxy,methylsulphonyloxy, ethylsulphonyloxy, n- or i-propylsulphonyloxy,represents in each case optionally fluorine- and/or chlorine-substitutedpropenyloxy, butenyloxy, propinyloxy or butinyloxy, or represents ineach case optionally nitro-, cyano-, fluorine-, chlorine-, bromine-,methyl-, ethyl-, n- or i-propyl-, trifluoromethyl-, methoxy-, ethoxy-,n- or i-propoxy, difluoromethoxy- or trifluoromethoxy-substitutedphenylmethoxy, phenylcarbonyloxy, phenylcarbonylmethoxy orphenylsulphonyloxy, R⁸ represents hydrogen, cyano, fluorine, chlorine,bromine, or represents in each case optionally fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, acetyl,propionyl, n- or i-butyroyl, methoxy, ethoxy, n- or i-propoxy,methoxycarbonyl, ethoxycarbonyl, n- or i-propoxycarbonyl, methylthio,ethylthio, n- or i-propylthio, methylsulphinyl, ethylsulphinyl,methylsulphonyl or ethylsulphonyl, R⁹ represents hydrogen, represents ineach case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, or representsoptionally fluorine-, chlorine- or methyl-substituted cyclopropyl, R¹⁰represents hydrogen, represents optionally fluorine-, chlorine-,methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl, orrepresents optionally fluorine-, chlorine- or methyl-substitutedcyclopropyl, and R¹¹ represents hydrogen, cyano, fluorine, chlorine,bromine, or represents in each case optionally fluorine-, chlorine-,methoxy-, or ethoxy-substituted methyl, ethyl, n- or i-propyl, methoxy,ethoxy, n- or i-propoxy, methoxycarbonyl, ethoxycarbonyl, n- ori-propoxycarbonyl, methylthio, ethylthio, n- or i-propylthio,methylsulphinyl, ethylsulphinyl, methylsulphonyl or ethylsulphonyl. 5.Compounds of the formula (I) according to claim 1, characterized in thatR¹ represents hydrogen, or represents in each case optionally fluorine-,chlorine-, methoxy- or ethoxy-substituted methyl, ethyl, n- or i-propyl,represents methoxy or ethoxy or represents the grouping —C(Q)-R², R²represents hydrogen, amino, hydrazino, or represents in each caseoptionally fluorine-, chlorine-, methoxy- or ethoxy-substituted methyl,ethyl or n- or i-propyl, represents dimethylamino, represents in eachcase optionally fluorine-, chlorine- or methyl-substituted cyclopropyl,cyclobutyl, cyclopentyl or cyclohexyl, represents in each caseoptionally nitro-, cyano-, fluorine-, chlorine-, bromine-methyl-,ethyl-, n- or i-propyl-, methoxy-, ethoxy- or n- ori-propoxy-substituted phenyl, phenylamino, phenylmethyl or phenylethyl,or represents in each case optionally nitro-, cyano-, fluorine-,chlorine-, bromine-, methyl-, ethyl-, difluoromethyl-, trifluoromethyl-,dichloromethyl-, trichloromethyl-, chlorodifluoromethyl-,fluorodichloromethyl-, methoxy-, ethoxy-, methylthio-, ethylthio-,difluoromethylthio-, trifluoromethylthio-, methoxycarbonyl-,ethoxycarbonyl-substituted furyl, furylmethyl, thienyl, thienylmethyl,pyrrolyl or pyrrolylmethyl, X represents hydrogen, nitro, fluorine,chlorine, bromine, methyl, ethyl or trifluoromethyl, Y representshydrogen, nitro, cyano, fluorine, chlorine, bromine, iodine, methyl,ethyl, difluoromethyl, trifluoromethyl, dichloromethyl, trichloromethyl,methoxymethyl, methylthiomethyl, methylsulphinylmethyl,methylsulphonylmethyl, methoxy, ethoxy, difluoromethoxy,trifluoromethoxy, methylthio, ethylthio, methylsulphinyl,ethylsulphinyl, methylsulphonyl, ethylsulphonyl ordimethylaminosulphonyl, R³ represents hydrogen or in each caseoptionally fluorine- and/or chlorine-substituted methyl or ethyl, R⁴represents hydroxyl, R⁵ represents hydrogen, fluorine, chlorine orrepresents in each case optionally fluorine- and/or chlorine-substitutedmethyl, ethyl, methoxy or ethoxy, R⁶ represents hydrogen or representsin each case optionally fluorine-, chlorine-, methoxy- orethoxy-substituted methyl, ethyl, n- or i-propyl, n-, i-, s- or t-butyl,R⁷ represents hydroxyl, or represents in each case optionally fluorine-,or chlorine-substituted methoxy or ethoxy, or represents optionallynitro-, cyano-, fluorine-, chlorine-, bromine, methyl-, ethyl-,trifluoromethyl-, methoxy- or ethoxy-substituted phenylmethoxy. 6.Process for preparing compounds of the formula I according to claim 1,characterized in that (a) compounds of the general formula (II)

in which A¹, A², R¹, X, Y and Z are as defined in claim 1, are reactedwith compounds of the general formula (III)

in which Q and R² are as defined in claim 1 and Q¹ represents halogen,alkoxy, alkylthio, aryloxy or arylthio, or, if appropriate, withcorresponding iso(thio)cyanates if appropriate in the presence of one ormore reaction auxiliaries and if appropriate in the presence of one ormore diluents, or that (b) carboxylic acids of the general formula (IV)

in which A¹, A², Q, R¹, R², X and Y are as defined in claim 1, orreactive derivatives thereof, such as, for example, corresponding acidhalides, acid cyanides or esters are reacted with compounds of thegeneral formula (V) H-Z   (V) in which Z is as defined in claim 1, ifappropriate in the presence of a dehydrating agent and also, ifappropriate in the presence of one or more reaction auxiliaries and, ifappropriate, in the presence of one or more diluents, or that (c)substituted benzoyl ketones of the general formula (Ia)

in which A¹, A², Q, R¹, R², R¹⁰, X and Y are as defined in claim 1, arereacted with an orthoformic ester or with a N,N-dimethyl-formamideacetal or with a cyanoformic ester or with carbon disulphide and analkylating agent and subsequently with hydroxylamine or an acid adductthereof, if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,or that (d) aryl ketones of the general formula (VI)

in which A¹, A², Q, R¹, X, Y and Z are as defined in claim 1 and Q²represents halogen, alkoxy, alkylthio, aryloxy or arylthio, or, ifappropriate, corresponding iso(thio)cyanates are reacted with compoundsof the general formula (VII) H—R²   (VII) in which R² is as defined inclaim 1, if appropriate in the presence of one or more reactionauxiliaries and if appropriate in the presence of one or more diluents,and following the practice of the process (a), (b), (c) or (d), theresulting compounds of the general formula (I) are, if appropriate,subjected to subsequent reactions according to customary methods forconversion into other compounds of the general formula (I).
 7. Compoundsof the formula (II)

in which A¹, A², R¹, X, Y and Z are as defined in claim
 1. 8. Processfor preparing compounds of the formula (II), characterized in thatcompounds of the general formula (VIII)

in which A¹, A², X, Y and Z are as defined in claim 1 and X¹ representshalogen, are reacted with ammonia or amino compounds of the generalformula (IX)

in which R¹ is as defined in claim 1, if appropriate in the presence ofa diluent and if appropriate under elevated pressure, at temperaturesbetween 0° C. and 100° C.
 9. Compounds of the formula (IV)

in which A¹, A², Q, R¹, R², X and Y are as defined in claim
 1. 10.Process for preparing compounds of the formula (IV), characterized inthat (α) compounds of the general formula (X)

in which A¹, A², Q, X and Y are as defined in claim 1 and R representshydrogen, an alkali metal or an alkaline earth metal equivalent oralkyl, are reacted with compounds of the general formula (VII) H—R²  (VII) in which R² is as defined in claim 1, if appropriate in thepresence of a diluent, at temperatures between 0° C. and 100° C.,followed, if appropriate, by using an ester hydrolysis customarymethods, or that (β) compounds of the general formula (XI)

in which A¹, A², R¹, X and Y are as defined in claim 1 and R representshydrogen, an alkali metal or an alkaline earth metal equivalent oralkyl, are reacted with (thi)oxo compounds of the general formula (III)

in which Q and R² are as defined in claim 1 and Q¹ represents halogen,alkoxy, alkylthio, aryloxy or arylthio, or, if appropriate, withcorresponding iso(thio)cyanates if appropriate in the presence of one ormore reaction auxiliaries and if appropriate in the presence of one ormore diluents, at temperatures between 0° C. and 100° C.
 11. Compoundsof the formula (Ia)

in which A¹, A², Q, R¹, R², R¹⁰, X and Y are as defined in claim
 1. 12.Herbicidal compositions, characterized in that they comprise at leastone compound according to any of claims 1 to 5 and customary extenders.13. Use of at least one compound according to any of claims 1 to 5 or acomposition according to claim 12 for controlling undesirable plants.14. Method for controlling undesirable plants, characterized in that atleast one compound according to any of claims 1 to 5 or a compositionaccording to claim 12 is allowed to act on the undesirable plants and/ortheir habitat.